Updated on 2025/04/15

Information

 

写真a

 
KUNINOBU YOICHIRO
 
Organization
Institute for Materials Chemistry and Engineering Department of Fundamental Organic Chemistry Professor
Kyushu University Platform of Inter/Transdisciplinary Energy Research (Concurrent)
Interdisciplinary Graduate School of Engineering Sciences Department of Interdisciplinary Engineering Sciences(Concurrent)
Title
Professor
Contact information
メールアドレス
Tel
0925838855
Profile
In our laboratory, we are trying to solve energy and environmental problems through creation of high performance catalysts, development of practical organic synthesis reactions, and creation of high-performance organic functional materials.
Homepage
  • https://kuninobu-lab-english.weebly.com/

    Homepage of Kuninobu Lab, Institute for Materials Chemistry and Engineering (Department of Molecular and Material Sciences, Interdisciplinary Graduate School of Engineering Sciences)

Research Areas

  • Nanotechnology/Materials / Structural organic chemistry and physical organic chemistry

  • Nanotechnology/Materials / Synthetic organic chemistry

Degree

  • Doctor of Science

Research History

  • Kyushu University Institute for Materials Chemistry and Engineering Professor 

    2017.2 - Present

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  • 2003年11月 岡山大学工学部物質応用化学科 助手 2005年4月 岡山大学大学院自然科学研究科機能分子化学専攻 助手(改組による) 2007年4月 岡山大学大学院自然科学研究科機能分子化学専攻 助教(職名変更による) 2012年4月 東京大学大学院薬学系研究科 ERATOプロジェクト グループリーダー(准教授相当) 2015年9月 ミュンスター大学(ドイツ) 客員教授   

Research Interests・Research Keywords

  • Research theme: Catalytic Reaction

    Keyword: Catalytic Reaction

    Research period: 2024

  • Research theme: Luminescent Material

    Keyword: Luminescent Material

    Research period: 2024

  • Research theme: Structural Organic Chemistry

    Keyword: Structural Organic Chemistry

    Research period: 2024

  • Research theme: Organometallic Chemistry

    Keyword: Organometallic Chemistry

    Research period: 2024

  • Research theme: Synthetic Organic Chemistry

    Keyword: Synthetic Organic Chemistry

    Research period: 2024

  • Research theme: Introduction of Fluorinated Functional Group

    Keyword: Introduction of Fluorinated Functional Group

    Research period: 2024

  • Research theme: pi-Conjugated System

    Keyword: pi-Conjugated System

    Research period: 2024

  • Research theme: C-H Bond Transformation

    Keyword: C-H Bond Transformation

    Research period: 2024

  • Research theme: We create novel transition metal catalysts which can realize high activity and selectivity, and develop highly efficient and practical synthetic organic reactions, such as C-H transformations. We also create high-performance organic functional materials, such as pi-conjugated molecules and polymers. We aim to solve energy and environmental problems through these projects.

    Keyword: Catalytic Reaction, Catalyst Design, C-H Bond Transformation, pi-Conjugated System, Polymer

    Research period: 2017.2

Awards

  • 日産化学・有機合成新反応/手法賞

    2023.12   有機合成化学協会   非共有結合性相互作用を活用する位置選択的な炭素-水素結合変換反応の開発

  • 2018 Albert Nelson Marquis Lifetime Achievement Award

    2018.4   Marquis Who's Who  

  • 2017 Albert Nelson Marquis Lifetime Achievement Award

    2017.4   Marquis Who's Who  

Papers

  • Bulky Bipyridine-Type Ligand-Enabled para-Selective C-H Borylation of Aromatic Compounds

    Enta Taisei、Yoshino Genki、Kuninobu Yoichiro

    ChemRxiv   N/A ( N/A )   N/A - N/A   2025.3

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.26434/chemrxiv-2025-2xm3m

    Repository Public URL: https://hdl.handle.net/2324/7347382

  • Host-Guest Interaction-Controlled Site-selective C-H Borylation of Aromatic Compounds

    Haotian Su ,Yoichiro Kuninobu

    ChemRxiv   N/A ( N/A )   N/A - N/A   2025.3

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.26434/chemrxiv-2025-n95d6

    Repository Public URL: https://hdl.handle.net/2324/7347379

  • Control of Multicolor and White Emissions by Tuning Equilibrium Between Fluorophores, Lewis Acids, and Their Complexes Using Polymers Reviewed International journal

    Mori, T.; Yoshigoe, Y.; Kuninobu, Y.

    Angew. Chem. Int. Ed.   58 ( 41 )   14457 - 14461   2019.10

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    DOI: 10.1002/anie.201903408

    Other Link: https://onlinelibrary.wiley.com/doi/full/10.1002/anie.201903408

  • Hydrogen Bond-Accelerated meta-Selective C-H Borylation of Aromatic Compounds and Expression of Functional Group and Substrate Specificities Reviewed

    Xu Lu, Yusuke Yoshigoe, Haruka Ida, Mitsumi Nishi, Motomu Kanai, Yoichiro Kuninobu

    ACS Catalysis   9 ( 3 )   1705 - 1709   2019.3

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    We found that meta-selective C-H borylation of aromatic compounds was accelerated when using urea moiety-containing bipyridine-type ligands unlike in cases involving a bipyridine-type ligand without the urea moiety. The acceleration was due to the recognition and capture of the aromatic substrates by the urea moiety of the ligand by hydrogen bonding. The acceleration was further enhanced by modifying the electronic and steric properties of the ligand. The functional group and substrate specificities were also observed using the urea moiety-containing ligands.

    DOI: 10.1021/acscatal.8b05005

  • Palladium-catalyzed synthesis of diaryl ketones from aldehydes and (hetero)aryl halides via C-H bond activation Reviewed

    Takayuki Wakaki, Takaya Togo, Daisuke Yoshidome, Yoichiro Kuninobu, Motomu Kanai

    ACS Catalysis   8 ( 4 )   3123 - 3128   2018.4

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    We developed a palladium-catalyzed C-H transformation that enabled the synthesis of ketones from aldehydes and (hetero)aryl halides. The use of picolinamide ligands was key to achieving the transformation. Heteroaryl ketones, as well as diaryl ketones, were synthesized in good to excellent yields, even in gram-scale, using this reaction. Results of density functional theory (DFT) calculations support the C-H bond activation pathway.

    DOI: 10.1021/acscatal.8b00440

  • Lewis Acid-Base Interaction-Controlled ortho-Selective C-H Borylation of Aryl Sulfides Reviewed International journal

    @Li, H.-L.; Kuninobu, Y.; @Kanai, M.

    Angew. Chem. Int. Ed.   56 ( 6 )   1495 - 1499   2017.2

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    DOI: 10.1002/anie.201610041

  • 4-Position-Selective C-H Perfluoroalkylation and Perfluoroarylation of Six-Membered Heteroaromatic Compounds Reviewed

    Masahiro Nagase, Yoichiro Kuninobu, Motomu Kanai

    Journal of the American Chemical Society   138 ( 19 )   6103 - 6106   2016.5

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    The first 4-position-selective C-H perfluoroalkylation and perfluoroarylation of six-membered heteroaromatic compounds were achieved using nucleophilic perfluoroalkylation and perfluoroarylation reagents. The regioselectivity was controlled by electrophilically activating the heteroaromatic rings, while sterically hindering the 2-position, with a sterically bulky borane Lewis acid. The reaction proceeded in good yield, even in gram scale, and by a sequential reaction without isolating the intermediates. This reaction could be applied to late-stage trifluoromethylation of a bioactive compound.

    DOI: 10.1021/jacs.6b01753

  • Erratum Rhodium-catalyzed asymmetric synthesis of spirosilabifluorene derivatives (Angewandte Chemie - International Edition (2013) (52) DOI: 10.1002/anie.201207723) Reviewed

    Yoichiro Kuninobu, Kanae Yamauchi, Naoya Tamura, Takayuki Seiki, Kazuhiko Takai

    Angewandte Chemie - International Edition   55 ( 6 )   1948   2016.2

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    DOI: 10.1002/anie.201511117

  • A meta-selective C-H borylation directed by a secondary interaction between ligand and substrate Reviewed

    Yoichiro Kuninobu, Haruka Ida, Mitsumi Nishi, Motomu Kanai

    Nature Chemistry   7 ( 9 )   712 - 717   2015.9

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    Regioselective C-H bond transformations are potentially the most efficient method for the synthesis of organic molecules. However, the presence of many C-H bonds in organic molecules and the high activation barrier for these reactions make these transformations difficult. Directing groups in the reaction substrate are often used to control regioselectivity, which has been especially successful for the ortho-selective functionalization of aromatic substrates. Here, we describe an iridium-catalysed meta-selective C-H borylation of aromatic compounds using a newly designed catalytic system. The bipyridine-derived ligand that binds iridium contains a pendant urea moiety. A secondary interaction between this urea and a hydrogen-bond acceptor in the substrate places the iridium in close proximity to the meta-C-H bond and thus controls the regioselectivity. 1 H NMR studies and control experiments support the participation of hydrogen bonds in inducing regioselectivity. Reversible direction of the catalyst through hydrogen bonds is a versatile concept for regioselective C-H transformations.

    DOI: 10.1038/nchem.2322

  • Benzylic C(sp3)-H Perfluoroalkylation of Six-Membered Heteroaromatic Compounds Reviewed

    Yoichiro Kuninobu, Masahiro Nagase, Motomu Kanai

    Angewandte Chemie - International Edition   54 ( 35 )   10263 - 10266   2015.8

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    Successful benzylic C(sp3)-H trifluoromethylation, pentafluoroethylation, and heptafluoropropylation of six-membered heteroaromatic compounds were achieved as the first examples of a practical benzylic C(sp3)-H perfluoroalkylation. In these reactions, BF2CnF2n+1 (n=1-3) functioned as both a Lewis acid to activate the benzylic position and a CnF2n+1 (n=1-3) source. The perfluoroalkylation proceeded at both terminal and internal positions of the alkyl chains. Perfluoroalkylated products were obtained in moderate to excellent yields, even on gram scale, and in a sequential procedure without isolation of the intermediates. By using this method, trifluoromethylation of a bioactive compound, as well as introduction of a CF3 group into a bioactive molecular skeleton, proceeded regioselectively.

    DOI: 10.1002/anie.201505335

  • Palladium-catalyzed oxirane-opening reaction with arenes via C-H bond activation Reviewed

    Zhen Wang, Yoichiro Kuninobu, Motomu Kanai

    Journal of the American Chemical Society   137 ( 19 )   6140 - 6143   2015.5

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    We achieved a palladium-catalyzed C-H activation/C-C coupling reaction between arenes with a pyridyl, aminoquinolinyl, imino, or amide directing group, and oxiranes. The reaction proceeded at room temperature without any additives and tolerated a wide variety of functional groups, and the products were obtained in good to excellent yields, even on gram scale. This is the first example of a transition-metal-catalyzed intermolecular direct coupling reaction between a C-H bond of aromatic compounds and a carbon atom of oxiranes via C-H bond activation. By using N-methoxybenzamide as a substrate, we obtained 3-substituted isochroman-1-ones in one pot. The coupling reaction proceeded with stereoretention. Kinetic isotope effect experiments suggested that C-H bond activation is the rate-determining step.

    DOI: 10.1021/jacs.5b02435

  • Copper-catalyzed intramolecular C(sp3)-H and C(sp2)-H amidation by oxidative cyclization Reviewed

    Zhen Wang, Jizhi Ni, Yoichiro Kuninobu, Motomu Kanai

    Angewandte Chemie - International Edition   53 ( 13 )   3496 - 3499   2014.3

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    The first copper-catalyzed intramolecular C(sp3)-H and C(sp 2)-H oxidative amidation has been developed. Using a Cu(OAc) 2 catalyst and an Ag2CO3 oxidant in dichloroethane solvent, C(sp3)-H amidation proceeded at a terminal methyl group, as well as at the internal benzylic position of an alkyl chain. This reaction has a broad substrate scope, and various β-lactams were obtained in excellent yield, even on gram scale. Use of CuCl2 and Ag2CO3 under an O2 atmosphere in dimethyl sulfoxide, however, leads to 2-indolinone selectively by C(sp2)-H amidation. Kinetic isotope effect (KIE) studies indicated that C-H bond activation is the rate-determining step. The 5-methoxyquinolyl directing group could be removed by oxidation. Silver ox: By using a Cu(OAc)2 catalyst and an Ag2CO3 oxidant in dichloroethane solvent, C(sp3)-H amidation proceeded at a terminal methyl group as well as at the internal benzylic position of an alkyl chain. This reaction has a broad substrate scope, and various β-lactams were obtained in excellent yield, even on a gram scale. Use of CuCl2 and Ag2CO3 under an O2 atmosphere led to 2-indolinone selectively synthesized by C(sp2)-H amidation. DMSO=dimethylsulfoxide.

    DOI: 10.1002/anie.201311105

  • Regioselective trifluoromethylation of N-heteroaromatic compounds using trifluoromethyldifluoroborane activator Reviewed

    Tomoaki Nishida, Haruka Ida, Yoichiro Kuninobu, Motomu Kanai

    Nature communications   5   2014.3

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    Many important drugs, agrochemicals and their lead compounds contain trifluoromethyl group(s). Most processes currently used to access trifluoromethyl group-containing molecules are performed by substitution of the carboxy or trichloromethyl groups using hazardous fluorinating reagents under harsh reaction conditions. Cross-coupling reactions between organohalides or boronic acids/esters and trifluoromethylating reagents are also used. Direct C-H trifluoromethylation of organic molecules, however, is the ideal method of introducing trifluoromethyl group(s). Despite the recent advances in C-H trifluoromethylation of N-heteroaromatic compounds, regioselective C-H trifluoromethylation of six-membered heteroaromatic compounds has yet to be achieved. Herein we present a general and reliable method for the synthesis of trifluoromethyl group-containing N-heteroaromatics through highly regioselective addition of a trifluoromethyl nucleophile to pyridine, quinoline, isoquinoline and two or three heteroatom-containing N-heteroaromatic N-oxides activated by trifluoromethyldifluoroborane. The C-H trifluoromethylation proceeds under mild conditions in gram scale with high functional group tolerance. This method will be useful in both laboratory and industrial processes.

    DOI: 10.1038/ncomms4387

  • Palladium-catalyzed Ci-H fluorosilylation of 2-phenylpyridines Synthesis of silafluorene equivalents Reviewed

    Qing Xiao, Xiangtai Meng, Motomu Kanai, Yoichiro Kuninobu

    Angewandte Chemie - International Edition   53 ( 12 )   3168 - 3172   2014.3

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    Treatment of 2-phenylpyridines with amino(1,3,2-dioxaborolan-2-yl) diphenylsilane produced fluorosilylated 2-phenylpyridines in good to excellent yields under palladium catalysis. This reaction is the first example of Ci-H fluorosilylation. Single-crystal X-ray structure analysis revealed a Lewis acid-base interaction between the silicon and nitrogen atoms, and the obtained fluorosilylated products are silafluorene equivalents. The fluorosilylated products showed stronger fluorescence than the corresponding silafluorene derivative. Treatment of 2-phenylpyridines with amino(1,3,2-dioxaborolan-2-yl) diphenylsilane produced fluorosilylated 2-phenylpyridines in good to excellent yields under palladium catalysis. This reaction is the first example of Ci-H fluorosilylation. A Lewis acid-base interaction exists between the silicon and nitrogen atoms, and the obtained fluorosilylated products can be regarded as silafluorene equivalents.

    DOI: 10.1002/anie.201310293

  • Rhenium-catalyzed synthesis of 3-imino-1-isoindolinones by C-H bond activation Application to the synthesis of polyimide derivatives Reviewed

    Shunsuke Sueki, Yuanfang Guo, Motomu Kanai, Yoichiro Kuninobu

    Angewandte Chemie - International Edition   52 ( 45 )   11879 - 11883   2013.11

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    Polyimide solution: Synthesis of the title compounds from aromatic imidates and isocyanates in good to excellent yields by a rhenium-catalyzed C-H bond transformation is described. The reaction also proceeded in high yield on gram scale and could be applied to the synthesis of polyimide derivatives (see figure), which are highly soluble in organic solvents.

    DOI: 10.1002/anie.201306360

  • Palladium-catalyzed ortho-selective C-H borylation of 2-phenylpyridine and its derivatives at room temperature Reviewed

    Yoichiro Kuninobu, Takashi Iwanaga, Tetsuya Omura, Kazuhiko Takai

    Angewandte Chemie - International Edition   52 ( 16 )   4431 - 4434   2013.4

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    Boron delivery: C-H borylation at the ortho-position of aromatic compounds is promoted by the treatment of 2-phenylpyridine, or its derivatives, with 9-borabicyclo[3.3.1]nonane in the presence of a palladium catalyst. This reaction proceeds at room temperature and can be conducted without the palladium catalyst at higher temperatures. In both cases, the regioselectivity is controlled by Lewis acid-base interaction between the boron and nitrogen atoms.

    DOI: 10.1002/anie.201210328

  • Rhodium-catalyzed asymmetric synthesis of spirosilabifluorene derivatives Reviewed

    Yoichiro Kuninobu, Kanae Yamauchi, Naoya Tamura, Takayuki Seiki, Kazuhiko Takai

    Angewandte Chemie - International Edition   52 ( 5 )   1520 - 1522   2013.1

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    Si goes chiral: Treatment of a bis(biphenyl)silane with a catalytic amount of a rhodium complex gave a spirosilabifluorene bearing a quaternary silicon atom. By using a rhodium catalyst with a chiral phosphine ligand (see scheme), asymmetric dehydrogenative cyclization proceeded to give chiral derivatives in good yields and enantioselectivities.

    DOI: 10.1002/anie.201207723

  • Manganese-catalyzed cleavage of a carbon-carbon single bond between carbonyl carbon and α-carbon atoms of ketones Reviewed

    Yoichiro Kuninobu, Tadamasa Uesugi, Atsushi Kawata, Kazuhiko Takai

    Angewandte Chemie - International Edition   50 ( 44 )   10406 - 10408   2011.10

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    Singled out: Treatment of ketones with carbodiimides in the presence of a catalytic amount of either [{HMn(CO)4}3] or [Mn 2(CO)10] gave amides in good to excellent yields. In this reaction, the carbon-carbon single bond of a ketone is cleaved efficiently. The reaction also proceeded by using isocyanates instead of carbodiimides.

    DOI: 10.1002/anie.201104704

  • Rhodium-catalyzed synthesis of silafluorene derivatives via cleavage of silicon-hydrogen and carbon-hydrogen bonds Reviewed

    Tomonari Ureshino, Takuya Yoshida, Yoichiro Kuninobu, Kazuhiko Takai

    Journal of the American Chemical Society   132 ( 41 )   14324 - 14326   2010.10

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    The rhodium-catalyzed synthesis of silafluorenes from biphenylhydrosilanes is described. This highly efficient reaction proceeds via both Si-H and C-H bond activation, producing only H2 as a side product. Using this method, a ladder-type bis-silicon-bridged p-terphenyl could also be synthesized.

    DOI: 10.1021/ja107698p

  • Rhenium-catalyzed regioselective alkylation of phenols Reviewed

    Yoichiro Kuninobu, Takashi Matsuki, Kazuhiko Takai

    Journal of the American Chemical Society   131 ( 29 )   9914 - 9915   2009.7

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    (Chemical Equation Presented) Treatment of phenol derivatives with terminal alkenes in the presence of a catalytic amount of a rhenium complex, Re 2(CO)10, gave monoalkylated phenol derivatives in good to excellent yields. This reaction proceeds at the ortho- or para-position of phenols regioselectively.

    DOI: 10.1021/ja904360k

  • Rhenium-catalyzed synthesis of stereodefined cyclopentenes from β-ketoesters and aliphatic allenes Reviewed

    Salprima Yudha S, Yoichiro Kuninobu, Kazuhiko Takai

    Angewandte Chemie - International Edition   47 ( 48 )   9318 - 9321   2008.11

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    (Chemical Equation Presented) Come on allene: Commercially available [Re2(CO)10] as a catalyst provides five-membered carbocycles in moderate to excellent yields with high stereoselectivity (see scheme). The configuration at each of the three sp3 carbon centers of the ring is defined. The reaction proceeds at the β, γ, and adjacent methylene positions of the allene; previously, similar reactions usually occurred at the α, β, and γ positions of the allene.

    DOI: 10.1002/anie.200803350

  • Synthesis of Cp-Re complexes via olefinic C-H activation and successive formation of cyclopentadienes Reviewed

    Yoichiro Kuninobu, Yuta Nishina, Takashi Matsuki, Kazuhiko Takai

    Journal of the American Chemical Society   130 ( 43 )   14062 - 14063   2008.10

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    Treatment of an α,β-unsaturated ketimine with an α,β-unsaturated carbonyl compound in the presence of a rhenium complex, Re2(CO)10, gave a cyclopentadienyl-rhenium complex. This reaction proceeds via rhenium-catalyzed C-H bond activation of an olefinic C-H bond, insertion of an α,β-unsaturated carbonyl compound into a Re-C bond of the alkenylrhenium intermediate, intramolecular nucleophilic cyclization, reductive elimination, elimination of aniline to give a cyclopentadiene derivative, followed by the formation of a cyclopentadienyl-rhenium complex from the cyclopentadiene derivative and the rhenium complex.

    DOI: 10.1021/ja805921f

  • Indium-catalyzed retro-claisen condensation Reviewed

    Atsushi Kawata, Kazumi Takata, Yoichiro Kuninobu, Kazuhiko Takai

    Angewandte Chemie - International Edition   46 ( 41 )   7793 - 7795   2007.10

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    (Chemical Equation Presented) Retro-aldol reaction: Indium-catalyzed reaction of a 1,3-diketone with an alcohol proceeds under solvent-free conditions by nucleophilic attack of the alcohol on a carbonyl group of the 1,3-diketone and carbon-carbon bond cleavage by a retro-Claisen condensation to give an ester in high yield (see scheme). Using water and an amine as nucleophiles instead of an alcohol gave the corresponding carboxylic acid and amide.

    DOI: 10.1002/anie.200702798

  • Manganese-catalyzed insertion of aldehydes into a C-H bond Reviewed

    Yoichiro Kuninobu, Yuta Nishina, Takahiro Takeuchi, Kazuhiko Takai

    Angewandte Chemie - International Edition   46 ( 34 )   6518 - 6520   2007.9

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    (Chemical Equation Presented) Mn gets in the game: In the presence of a manganese catalyst and a stoichiometric amount of hydrosilane, aldehydes insert into C-H bonds of aromatic rings of compounds with directing groups (see scheme). This first example of a manganese-catalyzed chemical transformation through C-H bond activation gives silyl ethers in good to excellent yields and can also be applied to asymmetric transformation.

    DOI: 10.1002/anie.200702256

  • Rhenium- and gold-catalyzed coupling of aromatic aldehydes with trimethyl(phenylethynyl)silane Synthesis of diethynylmethanes Reviewed

    Yoichiro Kuninobu, Eri Ishii, Kazuhiko Takai

    Angewandte Chemie - International Edition   46 ( 18 )   3296 - 3299   2007.6

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    (Chemical Equation Presented) Very couply! Coupling reactions of propargyl or benzyl alcohols with allyl- or alkynylsilanes proceed efficiently using [{ReBr(CO)3(thf)}2] as catalyst. Additionally, diethynylmethane derivatives were obtained by the reaction of aromatic aldehydes with trimethyl(phenylethynyl)silane in the presence of both the rhenium complex and AuCl (see scheme).

    DOI: 10.1002/anie.200700183

  • Efficient catalytic insertion of acetylenes into a carbon-carbon single bond of nonstrained cyclic compounds under mild conditions Reviewed

    Yoichiro Kuninobu, Atsushi Kawata, Kazuhiko Takai

    Journal of the American Chemical Society   128 ( 35 )   11368 - 11369   2006.9

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    A rhenium complex, [ReBr(CO)3(thf)]2, catalyzes the reaction of a 1,3-dicarbonyl cyclic compound with an acetylene to give a medium-sized cyclic compound in excellent yield. By using isocyanide as an additive, the catalytic activity of the rhenium complex changes dramatically, and the insertion of acetylenes into a carbon-carbon single bond occurs under mild conditions. A plausible mechanism is that the reaction proceeds via the formation of a rhenacyclopentene intermediate, ring opening by a retro-aldol reaction, isomerization, and reductive elimination.

    DOI: 10.1021/ja064022i

  • Rhenium-catalyzed insertion of aldehyde into a C-H bond Synthesis of isobenzofuran derivatives Reviewed

    Yoichiro Kuninobu, Yuta Nishina, Chie Nakagawa, Kazuhiko Takai

    Journal of the American Chemical Society   128 ( 38 )   12376 - 12377   2006.9

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    A rhenium complex, [ReBr(CO)3(thf)]2, catalyzed reactions of aromatic ketimines with aldehydes to give isobenzofuran derivatives in good to excellent yields. In contrast to ruthenium and rhodium catalysts, aldehydes, which are polar unsaturated molecules, inserted into the C-H bond after activation by the rhenium complex.

    DOI: 10.1021/ja065643e

  • Rhenium- and aniline-catalyzed one-pot annulation of aromatic ketones and α,β-unsaturated esters initiated by C-H bond activation Reviewed

    Yoichiro Kuninobu, Yuta Nishina, Makoto Shouho, Kazuhiko Takai

    Angewandte Chemie - International Edition   45 ( 17 )   2766 - 2768   2006.4

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    (Chemical Equation Presented) Several reaction steps, including C-H activation, lead to indene derivatives in good yields in the rhenium-catalyzed reaction of aromatic ketimines and ethyl acrylate. Indene derivatives can also be obtained by the reactions of aromatic ketones with α,β-unsaturated esters in the presence of a catalytic rhenium complex and p-anisidine (see scheme).

    DOI: 10.1002/anie.200503627

  • Insertion of polar and nonpolar unsaturated molecules into carbon-rhenium bonds generated by C-H bond activation Synthesis of phthalimidine and indene derivatives Reviewed

    Yoichiro Kuninobu, Yukimi Tokunaga, Atsushi Kawata, Kazuhiko Takai

    Journal of the American Chemical Society   128 ( 1 )   202 - 209   2006.1

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    A rhenium complex, [ReBr(CO)3(thf)]2, catalyzes the reaction of an aromatic aldimine with an isocyanate and an acetylene to give a phthalimidine and an indene derivative in a quantitative yield, respectively. The reactions proceed via C-H bond activation, insertion of the isocyanate or the acetylene, Intramolecular nucleophilic cyclization to the aldimine of the generated amido- or alkenyl-rhenium species, and reductive elimination. In contrast to ruthenium and rhodium catalysts, which are usually employed in this type of reaction, the rhenium catalyst promotes the insertion of a polar unsaturated molecule. This occurs more easily than the insertion of a nonpolar unsaturated molecule.

    DOI: 10.1021/ja054216i

  • Rhenium-catalyzed formation of indene frameworks via C-H bond activation [3+2] Annulation of aromatic aldimines and acetylenes Reviewed

    Yoichiro Kuninobu, Atsushi Kawata, Kazuhiko Takai

    Journal of the American Chemical Society   127 ( 39 )   13498 - 13499   2005.10

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    A rhenium complex, [ReBr(CO)3(thf)]2, catalyzes the reaction of an aromatic aldimine with an acetylene to give an indene derivative in a quantitative yield. The reaction proceeds via C-H bond activation, insertion of the acetylene, intramolecular nucleophilic cyclization, and reductive elimination. In contrast to ruthenium and rhodium catalysts, which are usually employed in this type of reaction, the rhenium catalyst promotes the intramolecular nucleophilic cyclization of the alkenylmetal species generated by insertion of the acetylene.

    DOI: 10.1021/ja0528174

  • Photoinduced Carbamoylarylation of Alkynes with N-Aryl Oxamic Acids.

    Sekine K, Yue G, Kajiwara J, Wu D, Shiozuka A, Kuninobu Y

    Organic letters   2025.4

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  • Ligand-enabled enantio- and site-selective remote C-H arylation of 2-(2-phenpropyl)pyridine derivatives Reviewed

    Li, DY; Li, JP; Yabu, S; Wang, LS; Sato, H; Higashi, M; Kuninobu, Y; Li, HL

    ORGANIC CHEMISTRY FRONTIERS   12 ( 7 )   2232 - 2241   2025.3   ISSN:2052-4129

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    The great potential of transition metal-catalyzed C-H functionalization lies in its ability to selectively target specific C-H bonds in complex molecules. Therefore, the development of enantio- and site-selective C-H functionalization is a long-term pursuit in this field. Herein, we disclose a ligand-enabled enantio- and site-selective remote C-H arylation of 2-(2-phenylpropyl)pyridine derivatives. The combination of an acetyl-protected aminoethyl phenyl thioether (MPA-thiol) with aryl iodides is found to enable γ-C(sp3)-H arylation, whereas l-pyroglutamic acid (l-pGlu) promotes δ-C(sp2)-H cross-coupling with various aryl-Bpin moieties. Notably, both C-H arylations proceed with high enantioselectivity and good yields. The results of DFT calculations support the enantioselectivity and site-selectivity of these two C-H arylations. Moreover the utility of this transformation was demonstrated by derivatization of a harmane alkaloid, a gram scale reaction and the successful removal of the pyridyl directing group.

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  • Hydrogen Bond-Controlled Site-Selective C(sp3)-H Alkylation of Sulfonanilides. Reviewed International journal

    Hui Jiang, Kohei Sekine, Yoichiro Kuninobu

    The Journal of organic chemistry   90 ( 9 )   3454 - 3467   2025.2   ISSN:0022-3263 eISSN:1520-6904

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    We successfully developed a decatungstate-catalyzed benzylic C(sp3)-H alkylation of sulfonanilides by utilizing the hydrogen bond between the sulfonamide group of the substrates and decatungstate photocatalysts. Using this catalytic system, site-selective C(sp3)-H alkylation was achieved at the benzylic position near the sulfonamide group.

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  • Divergent Synthesis of Silacycles by Ligand-Controlled Rhodium-Catalyzed Annulation of (2-Hydrosilylaryl)acetylenes. International journal

    Kazuto Fuji, Kyohei Kawashima, Toshifumi Mori, Kohei Sekine, Yoichiro Kuninobu

    Organic letters   27 ( 7 )   1614 - 1619   2025.2   ISSN:1523-7060 eISSN:1523-7052

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    This study demonstrates the rhodium-catalyzed divergent synthesis of 5-, 5,6-, and 8-membered silacyclic compounds, such as benzosilole, silolosiline, and disilocine, from (2-hydrosilylaryl)acetylenes. To achieve high product selectivity, intra- and intermolecular reactions are controlled by tuning the mono- and bidentate phosphine ligands on the rhodium catalyst precursor. Deuterium labeling experiments and computational studies reveal that the annulation reaction proceeds via hydride transfer to the alkyne moiety.

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  • Development of Site-Selective C-H Transformations Using Noncovalent Interaction

    Kuninobu Yoichiro

    Journal of Synthetic Organic Chemistry, Japan   82 ( 10 )   954 - 964   2024.10   ISSN:00379980 eISSN:18836526

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    <p>The control of site-selectivity is important to obtain the desired products efficiently in synthetic organic chemistry. Because there are many C-H bonds with similar reactivities in organic molecules, it was difficult to promote site-selective C-H transformations without using directing groups. In this award article, I describe new strategies to control site-selectivity in C-H transformations using noncovalent interactions, such as hydrogen bond, Lewis acid-base interaction and electrostatic interaction, between the catalyst and the substrate. As a result, highly site-selective C-H transformations have been achieved. By using Lewis acid-base interaction between the substrate and reagent, <i>ortho</i>-selective C(sp<sup>2</sup>)-H borylation and silylation were achieved. In addition, site-selective C(sp<sup>2</sup>)-H trifluoromethylation was developed by inclusion of the aromatic substrate into cyclodextrin by supramolecular interaction.</p>

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  • Mechanistic insights into the role of cyclodextrin in the regioselective radical C-H trifluoromethylation of aromatic compounds

    Kawashima, K; Lu, X; Kuninobu, Y; Mori, T

    JOURNAL OF COMPUTATIONAL CHEMISTRY   45 ( 25 )   2112 - 2118   2024.9   ISSN:0192-8651 eISSN:1096-987X

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    The regioselective radical C-H trifluoromethylation of aromatic compounds have been shown to proceed in good yield and high regioselectivity when cyclodextrin (CD) is present. Yet, the reaction mechanism and the role of CD during the reaction have remained obscure. To this end, here we performed density functional theory (DFT) calculations to the conformations obtained by semiempirical quantum mechanical molecular dynamics calculations to reveal the reaction mechanism and the role of CD in controlling regioselectivity. The results show that metal salt increases the yield but do not affect the regioselectivity, which we further confirmed by an experiment. In contrast, multiple CD-substrate complex conformations and reaction pathways were obtained, and CD was shown to contribute to improving the regioselectivity by stabilizing the intermediate state via encapsulation. The present study indicates that CDs can increase the regioselectivity by stabilizing the intermediate and product states while only marginally affecting the transition state.

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  • Gold-Catalyzed Synthesis of 5H-Benzo[b]indeno[2,1-d]silines by Insertion of Vinyl Carbocations into the Si-H Bond. International journal

    Kohei Sekine, Kazuto Fuji, Kyohei Kawashima, Toshifumi Mori, Yoichiro Kuninobu

    Chemistry - A European Journal (Weinheim an der Bergstrasse, Germany)   30 ( 65 )   e202403163   2024.9   ISSN:0947-6539 eISSN:1521-3765

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    We have developed a gold-catalyzed cascade reaction of aryldiynes bearing a hydrosilyl group to afford a variety of unexplored 5H-benzo[b]indeno[2,1-d]silines. The reaction system is applicable to the synthesis of bidirectionally π-extended silacycles from tetra(alkynyl)aryl compounds. Computational studies suggest that 5H-benzo[b]indeno[2,1-d]silines are formed via the insertion of a vinyl carbocation intermediate into the Si-H bond.

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  • Synthesis of a novel twisted π-conjugated macrocycle <i>via</i> double Friedel-Crafts reaction and its physical properties Reviewed

    Jiang, ZY; Kuninobu, Y

    CHEMICAL COMMUNICATIONS   60 ( 59 )   7642 - 7645   2024.7   ISSN:1359-7345 eISSN:1364-548X

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    We synthesized a cyclic molecule from diarylalkynes and Meldrum's acid derivatives as the methylenation reagent via double Friedel-Crafts reaction. Single-crystal X-ray structure analysis confirmed the twisted structure of the molecule. We also investigated their physical properties and homoconjugation by UV-Vis, photoluminescence, DFT and TD-DFT calculations.

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  • Synthesis and Properties of Cyclic π-Conjugated Molecules and Their Dication and Monoradical Cation Reviewed

    Xu, RJ; Kuninobu, Y

    ORGANIC LETTERS   26 ( 26 )   5582 - 5586   2024.6   ISSN:1523-7060 eISSN:1523-7052

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    We synthesized cyclic π-conjugated molecules by double Friedel−Crafts reaction of amino group-substituted 1,2-bis(2-phenylethynyl)benzene with Meldrum’s acid derivative. The structures of the cyclic π-conjugated molecules were determined by single-crystal X-ray structure analysis. The oxidation of the dimethylamino group-substituted π-conjugated molecule with NOBF4 gave a closed-shell dication that is stable at >210 °C. The monoradical cation of the di(4-methoxyphenyl)amino group-substituted π-conjugated molecule is stable in dichloromethane solution (half-life of nearly 15 days) and shows near-infrared absorption.

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  • Boronyl-Group-Assisted Decatungstate-Catalyzed Benzylic C(sp<sup>3</sup>)–H Alkylation Reviewed

    Hui Jiang, Takeru Torigoe, Yoichiro Kuninobu

    Organic Letters   26 ( 23 )   4853 - 4856   2024.6   ISSN:1523-7060 eISSN:1523-7052

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    Boronic acid synthesis primarily involves the introduction of boronyl groups. However, an alternative route that involves the functionalization of boronic acids has not received much attention. This study describes the catalytic C(sp3)-H alkylation of ortho-tolylboronic acids utilizing the interaction between a free boronyl group [−B(OH)2] and a decatungstate photocatalyst [W10O32]4-. The boronyl groups of the alkylated products could be converted without isolation of the alkylated product.

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  • Carbamoylarylation of Alkenes with N-Aryl Oxamic Acids Involving 1,4-Aryl Migration Via C(aryl)-N Bond Cleavage

    Akira Shiozuka, Di Wu, Kyohei Kawashima, Toshifumi Mori, Kohei Sekine, Yoichiro Kuninobu

    ACS Catalysis   14 ( 8 )   5972 - 5977   2024.4   ISSN:2155-5435 eISSN:2155-5435

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    We report carbamoylarylation of alkenes using N-aryl oxamic acid derivatives under visible-light irradiation. Reactions of alkenes with carbamoyl radicals generated using N-aryl oxamic acid derivatives to afford Giese-type products or 3,4-dihydroquinolin-2(1H)-ones via ortho-radical addition to an aryl amide moiety have been previously reported. However, this study reveals that the introduction of a removable bulky group onto the nitrogen atom of N-aryl oxamic acids facilitates the radical addition of carbamoyl radicals to alkenes, resulting in 1,4-aryl migration via C(aryl)-N bond cleavage, thus affording arylpropanamides. Various alkenes, such as acrylic acid and styrene derivatives, are successfully applied to the synthesis of a variety of arylpropanamide derivatives, including 1,4-dicarbonyl amides, forming two C-C bonds.

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  • Carbamoylarylation of Alkenes with N-Aryl Oxamic Acids Involving 1,4-Aryl Migration Via C(aryl)–N Bond Cleavage Reviewed International journal

    Shiozuka, A.; Wu, D.; Kawashima, K.; Mori, T.; Sekine, K.; Kuninobu, Y.

    ACS Catal.   14   5972 - 5977   2024.4

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  • 5‐Ammonium‐4,4‐dimethylvaleryl (Amv) Group: Generation from Acryloyl Group through Decatungstate‐Catalyzed C(sp<sup>3</sup>)−H Addition and Removal by Base‐Triggered Cyclization Reviewed International journal

    Song, J.; Torigoe, T.*; Kuninobu, Y.*

    Eur. J. Org. Chem.   2023 ( 46 )   e202301015   2023.12   ISSN:1434-193X eISSN:1099-0690

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    Abstract

    The 5‐ammonium‐4,4‐dimethylvaleryl (Amv) group was generated by conversion of acryloyl group through decatungstate‐catalyzed addition of C(sp<sup>3</sup>)−H bond of i‐BuNH<sub>2</sub>⋅HCl under the irradiation of UV light (365 nm or 405 nm). Treatment of Amv‐protected alcohols and anilines with aqueous Na<sub>2</sub>CO<sub>3</sub> promoted the efficient deprotection of Amv. This is a unique method for the efficient removal of acryloyl groups from phenols, alcohols, and anilines. The selective removal of acryloyl groups through Amv in the presence of another acetyl or benzoyl group was demonstrated. The base‐triggered intramolecular cyclization of Amv was monitored by the release of a fluorescent molecule, and it was found that cyclization by Na<sub>2</sub>CO<sub>3</sub> was very rapid (within 1 min) and that some weak bases such as 2,6‐lutidine are sufficient to promote cyclization.

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  • Non-covalent Interaction-Controlled Site-selective C-H Transformations

    Kuninobu, Y

    CHEMICAL RECORD   23 ( 10 )   e202300149   2023.10   ISSN:1527-8999 eISSN:1528-0691

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    Site-selective C−H transformations are important to obtain desired compounds as single products in a highly efficient manner. However, it is generally difficult to achieve such transformations because organic substrates contain many C−H bonds with similar reactivities. Therefore, the development of practical and efficient methods for controlling site selectivity is highly desirable. The most frequently used strategy is “directing group method”. Although this method is highly effective and promotes site-selective reactions, it has several limitations. Our group recently reported other methods to achieve site-selective C−H transformations using non-covalent interactions between a substrate and a reagent or a catalyst and a substrate (non-covalent method). In this personal account, the background of site-selective C−H transformations, our reaction design to achieve site-selective C−H transformations, and recently reported reactions are explained.

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  • Regioselective C-H Trifluoromethylation and Its Related Reactions of (Hetero)aromatic Compounds

    Kuninobu, Y

    CHEMICAL RECORD   23 ( 9 )   e202300003   2023.9   ISSN:1527-8999 eISSN:1528-0691

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    Fluorinated functional groups, including trifluoromethyl group, play important roles in the development of drugs, agrochemicals, and organic functional materials. Therefore, the development of highly effective and practical reactions to introduce fluorinated functional groups into (hetero)aromatic compounds is highly desirable. We have achieved several regioselective C−H trifluoromethylation and related reactions by electrophilic and nucleophilic activation of six-membered heteroaromatic compounds and steric protection of aromatic compounds. These reactions proceed in good to excellent yields, even on a gram scale, with high functional group tolerance, and are applicable to the regioselective trifluoromethylation of drug molecules. In this personal account, the background of the introduction reactions of fluorinated functional groups, our reaction designs to achieve regioselective C−H trifluoromethylation and the related reactions of (hetero)aromatic compounds are explained.

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  • Site-selective Direct Intermolecular C(sp3)–H Alkylation of Saccharides and Switching of Reaction Sites by Changing Photocatalysts Reviewed International journal

    Li, Y.; Kuninobu, Y.*

    Adv. Synth. Catal.   365 ( 15 )   2577 - 2587   2023.7   ISSN:1615-4150 eISSN:1615-4169

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    We developed a site-selective intermolecular C(sp3)−H alkylation of saccharides with electron-deficient alkenes using photocatalysis by anthraquinone and tetrabutylammonium decatungstate (TBADT). The main reaction site of anthraquinone-catalyzed C(sp3)−H alkylation is determined by the weakness of the C−H bond. The reaction site can be switched by changing the photocatalyst to TBADT, and the site-selectivity is controlled by the steric hindrance between the bulkier TBADT photocatalyst and the substituents of the saccharides. The reaction is compatible with several electron-deficient alkenes and saccharides, and provides C-saccharides in good yields. Furthermore, the monoalkylated product was obtained in excellent yield, even on the gram scale, under TBADT photocatalysis. Applicability was demonstrated by site-selective C(sp3)−H alkylation of glycosyl derivatives. The reactions proceed via a site-selective hydrogen atom transfer between the photocatalyst and saccharide, and the generated carbon radical reacts with an electron-deficient alkene to give alkylated products.

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  • Decatungstate-Catalyzed C(sp3)–H Alkylation of a Val Residue Proximal to the N-Terminus Controlled by an Electrostatic Interaction Reviewed International journal

    Song, J.; Torigoe, T.*; Kuninobu, Y.*

    Org. Lett.   25 ( 20 )   3708 - 3712   2023.5   ISSN:1523-7060 eISSN:1523-7052

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    The decatungstate photocatalyst [W10O32]4-efficiently promoted the C(sp3)-H alkylation of the trifluoroacetic acid salt of valine methyl ester (H-Val-OMe·TFA) with electron-deficient alkenes under UV irradiation. The electrostatic interaction between the cationic ammonium group (+NH3) of the main chain and anionic [W10O32]4-played an important role in this reaction. The influence of various protected amino acids in the C(sp3)-H alkylation was investigated as the model reaction for the alkylation of Val-containing peptides. The introduction of an alkyne moiety into Val through this alkylation was successful, and successive copper-catalyzed azide-alkyne cycloaddition (CuAAC) was demonstrated. The C(sp3)-H bond of a Val residue located at the second from the N-terminus was also successfully converted. C(sp3)-H alkylation of oligopeptides containing two Val residues selectively proceeded proximally to the N-terminus.

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  • Bifunctional 1-Hydroxypyrene Photocatalyst for Hydrodesulfurization via Reductive C(Aryl)-S Bond Cleavage Reviewed International journal

    Wu, D.; Shiozuka, A.; Kawashima, K.; Mori, T. Sekine, K.*; Kuninobu, Y.*

    Org. Lett.   25 ( 18 )   3293 - 3297   2023.4   ISSN:1523-7060 eISSN:1523-7052

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    We developed the visible-light-induced hydrodesulfurization of alkyl aryl thioethers via the reductive cleavage of the C(aryl)-S bond using 1-hydroxypyrene as a Brønsted acid-reductant bifunctional photocatalyst. The hydrodesulfurization reaction proceeded under simple reaction conditions (1-hydroxypyrene and Et3N in THF under purple LED illumination); this reaction did not require chemicals commonly used for hydrodesulfurization, such as hydrosilanes, transition metal catalysts, and/or stoichiometric amounts of metal reagents. Detailed mechanistic studies based on control experiments, spectroscopic measurements, and computational studies revealed that the cleavage of the C(aryl)-S bond and the formation of the C(aryl)-H bond proceeded via the formation of the ion pair between the radical anion of alkyl aryl thioether and Et3N+H, resulting in the generation of a sulfur radical. In addition, the 1-hydroxypyrene catalyst was regenerated via hydrogen atom transfer (HAT) from Et3N.

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  • 3-Position-Selective C–H Trifluoromethylation of Pyridine Rings Based on Nucleophilic Activation Reviewed International journal

    Muta, R.; Torigoe, T.; Kuninobu, Y.*

    Org. Lett.   24 ( 44 )   8218 - 8222   2022.11   ISSN:1523-7060 eISSN:1523-7052

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    The first example of the 3-position-selective C(sp2)-H trifluoromethylation of pyridine rings was established. 3-Position-selective trifluoromethylation was achieved by the nucleophilic activation of pyridine and quinoline derivatives through hydrosilylation and successive electrophilic trifluoromethylation of the enamine intermediate. This reaction was applicable to perfluoroalkylation at the 3 position of the pyridine rings and late-stage trifluoromethylation of a bioactive molecule. Mechanistic studies indicated that the reaction proceeds via the formation of N-silyl enamine and trifluoromethylated enamine intermediates.

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  • Near-Infrared and Dual Emissions of Diphenylamino Group-Substituted Malachite Green Derivatives Reviewed International journal

    Mori, T.; Sekine, K.; Kawashima, K.; Mori, T.; Kuninobu, Y.*

    Eur. J. Org. Chem.   2022 ( 31 )   e202200873   2022.7   ISSN:1434-193X eISSN:1099-0690

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    Novel triarylmethanols and triarylmethyl cations with diphenylamino groups were designed and synthesized. The triarylmethyl cations exhibited near-infrared (NIR) emission in toluene solution, solid film state, and polystyrene (PS) film. The emission intensities of the triarylmethyl cations were strongest in the PS film. The relative quantum yield of the PS film increased as the number of diphenylamino groups increased. In addition, triarylmethanols exhibit dual emission in their aggregated state owing to the intermolecular interactions between triphenyl amine moieties and/or hydroxy groups. These findings are interesting because NIR and dual emissions are not observed in the dimethylamino group-substituted triarylmethyl cation, which is referred to as the "malachite green," and the corresponding triarylmethanol, respectively.

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  • Photoinduced Divergent Deaminative Borylation and Hydrodeamination of Primary Aromatic Amines Reviewed International journal

    Shiozuka, A.; Sekine, K.*; Toki, T.; Kawashima, K.; Mori, T.*; Kuninobu, Y.*

    Org. Lett.   24 ( 23 )   4281 - 4285   2022.6   ISSN:15237060 eISSN:15237052

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    We have developed the divergent deaminative borylation and hydrodeamination of primary aromatic amines using bis(pinacolato)diboron. These transformations can be switched by the reaction conditions. Mechanistic and computational studies have suggested that the cleavage of the C–N bond and the formation of C–B bond are unlikely to involve free aryl radical intermediates. However, hydrodeamination is shown to proceed via hydrogen atom transfer between the corresponding aryl radical and an ethereal solvent.

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  • Iridium-catalyzed C(sp3)–H Borylation Using Silyl-Bipyridine Pincer Ligands Reviewed International journal

    Kawazu, R.; Torigoe, T.*; Kuninobu, Y.*

    Angew. Chem. Int. Ed.   61 ( 22 )   e202202327   2022.5   ISSN:1433-7851 eISSN:1521-3773

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    New ligands for the iridium-catalyzed C(sp3)−H borylation of aliphatic compounds were established. In sharp contrast to 6-methyl-2,2′-bipyridine and 6-isobutyl-2,2′-bipyridine, 2,2′-bipyridine and 1,10-phenanthroline derivatives bearing a hydrosilylmethyl group (which would give a thermally stable NNSi pincer complex) served as suitable ligands for the reaction. Among them, a phenanthroline-based NNSi pincer ligand was shown to be an excellent ligand, and various aliphatic compounds were efficiently converted to the corresponding borylated products using the Ir/NNSi pincer catalyst system. The NNSi pincer ligand showed unique selectivity and enabled the iridium-catalyzed C(sp3)−H borylation using pinacolborane [H−B(pin)] instead of B2(pin)2. The formation of an iridium complex bearing a quinoline-based NNSi pincer ligand from [IrCl(cod)]2 was observed, and the catalytic activity of the complex was demonstrated.

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  • Creation of Transition Metal Catalysts with Substrate Recognition Moiety and Development of Regioselective and Substrate Specific Reactions. Invited Reviewed

    Kuninobu, Y.*

    J. Synth. Org. Chem. Jpn.   80 ( 5 )   421 - 430   2022.5   ISSN:00379980 eISSN:18836526

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    <p>Regiocontrol is very important to obtain the desired products efficiently in synthetic organic chemistry. Because there are many C-H bonds with similar reactivities in organic molecules, it was difficult to promote regioselective C-H transformations without using directing groups. In this account, I describe a new strategy to control regioselectivities in C-H transformations using noncovalent interactions, such as hydrogen bond and Lewis acid-base interaction, between the catalyst and the substrate. As a result, highly regioselective C-H transformations have been achieved. By using the catalytic system, the rate of the C-H transformation was accelerated and the yield of the product was improved dramatically. In addition, the substrate and functional group specificities were expressed.</p>

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  • Photoinduced Organic Reactions by Employing Pyrene Catalysts Invited Reviewed International journal

    Shiozuka, A.; Sekine, K.*; Kuninobu, Y.*

    Synthesis   54 ( 10 )   2330 - 2339   2022.2   ISSN:0039-7881 eISSN:1437-210X

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    Pyrene is one of the most attractive polycyclic aromatic hydrocarbons (PAHs) in photochemistry. Based on their redox properties, pyrenes have potential as photosensitizers. In this review, we summarize recent developments in pyrene-catalyzed photoinduced organic reactions occurring via energy transfer or single-electron transfer based on the excited state of the pyrene.

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  • Palladium-Catalyzed Enantioselective C(sp3)–H Arylation of 2-Propyl Azaaryls Enabled by Amino Acid Ligand. Reviewed International journal

    Li, H.-L.*; Yang, D.-F.; Jiang, H.-Q.; Antilla, J. C.*; Kuninobu, Y.*

    Org. Lett.   24 ( 6 )   1286 - 1291   2022.2   ISSN:1523-7060 eISSN:1523-7052

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    A palladium(II)-catalyzed enantioselective arylation of unbiased secondary C(sp3)-H bonds was developed. The enantioselectivity was controlled by the combination of a pyridyl or isoquinolinyl directing group and an amino acid, N-Boc-2-pentyl proline. A variety of 2-propyl azaaryls and biaryl iodides were employed to provide arylated products in moderate to good yields (up to 82%) with high enantioselectivities (up to 93:7 er). This reaction is a rare example of an amino-acid-enabled enantioselective acyclic methylene C(sp3)-H arylation. Furthermore, the reaction proceeded with high enantioselectivity even on a gram scale, and the product was transformed to a 5,6,7,8-tetrahydroisoquinoline bioactive molecule. Kinetic isotope effect (KIE) experiments indicated that C-H activation is the rate-determining step for the enantioselective C(sp3)-H arylation.

    DOI: 10.1021/acs.orglett.1c04215

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  • Control of Site-Selectivity in Hydrogen Atom Transfer by Noncovalent Interactions: Proximal-Selective C(sp3)–H Alkylation of 2-Methylanilinium Salts Using a Decatungstate Photocatalyst. Reviewed International journal

    Zhen, J.; Torigoe, T.*; Kuninobu, Y.*

    ACS Catal.   12 ( 5 )   3058 - 3062   2022.2   ISSN:2155-5435

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    Site-selective C(sp3)-H alkylation of 2-methylanilinium salts via radical intermediates was developed. The anionic decatungstate photocatalyst ([W10O32]4-) interacts with the ammonium group of the substrate through electrostatic interaction and selectively abstracts a hydrogen atom from the proximal benzylic carbon atom under UV irradiation. A variety of 2-methylanilinium salts reacted with electron-deficient alkenes. The alkylated product was successfully converted into an aryl iodide via cleavage of the C-N bond and a tetrahydrobenzoazepinone derivative by intramolecular cyclization. Mechanistic studies clearly show the existence of the interactions between [W10O32]4- and the ammonium group.

    DOI: 10.1021/acscatal.2c00278

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  • Synthesis of fluorenes and their related compounds from biaryls and Meldrum's acid derivatives Reviewed International journal

    Jiang, Z.; Sekine, K.; Kuninobu, Y.*

    Chem. Commun.   58 ( 6 )   843 - 846   2021.12   ISSN:1359-7345 eISSN:1364-548X

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    A new synthetic method for preparing fluorenes from amino group-containing biaryls and Meldrum's acid derivatives was developed. The reaction proceeded without a catalyst and loss of functional groups. The corresponding six- and seven-membered cyclic products were obtained using biaryl ether and ortho-terphenyl as substrates, respectively.

    DOI: 10.1039/d1cc06212c

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  • Facile Synthesis of Tribenzosilepins from Terphenyls and Dihydrosilanes by Electrophilic Double Silylation Invited Reviewed International journal

    Dong, Y.; Sekine, K.; Kuninobu, Y.*

    Chem. Commun.   57 ( 57 )   7007 - 7010   2021.6

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    DOI: 10.1039/D1CC02326H

  • Photoinduced Deaminative Borylation of Unactivated Aromatic Amines Enhanced by CO2 Invited Reviewed International journal

    Shiozuka, A.; Sekine, K.*; Kuninobu, Y.*

    Org. Lett.   23 ( 12 )   4774 - 4778   2021.6

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    DOI: 10.1021/acs.orglett.1c01503

  • Regioselective C-H Trifluoromethylation of Aromatic Compounds​ by Inclusion in Cyclodextrins Reviewed International journal

    Lu, X.; Kawazu, R.; Song, J.; Yoshigoe, Y.; Torigoe, T.; Kuninobu, Y.*

    Org. Lett.   23 ( 11 )   4327 - 4331   2021.5

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    DOI: 10.1021/acs.orglett.1c01259

  • Manganese/Bipyridine-catalyzed Non-directed C(sp3)–H Bromination Using NBS and TMSN3. Invited Reviewed International journal

    Sneh, K.; Torigoe, T.; Kuninobu, Y.*

    Beilstein J. Org. Chem.   17   885 - 890   2021.4

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    DOI: 10.3762/bjoc.17.74

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  • Urea-accelerated Iridium-catalyzed 2-Position-selective C-H Borylation of Indole Derivatives. Reviewed International journal

    Wang, J.; Torigoe, T.; Kuninobu, Y.*

    Chem. Lett.   50   808 - 811   2021.4

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    DOI: 10.1246/cl.200939

    Other Link: https://www.journal.csj.jp/doi/full/10.1246/cl.200939

  • Regioselective C(sp3)–H Alkylation of Fructopyranose Derivative by 1,6 HAT. Reviewed International journal

    Li, Y.; Miyamoto, S.; Torigoe, T.; Kuninobu, Y.*

    Org. Biomol. Chem.   19   3124 - 3127   2021.4

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    DOI: 10.1039/d1ob00326g

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  • C–N and C–O Bond Formation in Copper-Catalyzed/Mediated sp3 C–H Activation: Mechanistic Studies from Experimental and Computational Aspects Reviewed International journal

    Yuhang Yang, Fei Cao, Linbin Yao, Tao Shi, Bencan Tang*, Yoichiro Kuninobu*, and Zhen Wang*

    J. Org. Chem.   85 ( 15 )   9713 - 9726   2020.7

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    DOI: 10.1021/acs.joc.0c01038

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  • Palladium-catalyzed Secondary C(sp3)-H Arylation of 2-Alkylpyridines Reviewed International journal

    Li, H.-L.: Kuninobu, Y.*; Antilla, J. C.*

    Adv. Synth. Catal.   362 ( 13 )   2637 - 2641   2020.5

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    DOI: 10.1002/adsc.202000306

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  • Iridium-Catalyzed ortho-C–H Borylation of Thioanisole Derivatives Using Bipyridine-Type Ligand Reviewed International journal

    Zeng, J.; Naito, M.; Torigoe, T.; Yamanaka, M.*; Kuninobu, Y.*

    Org. Lett.   22 ( 9 )   3485 - 3489   2020.4

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    DOI: 10.1021/acs.orglett.0c00946

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  • Synthesis, Structures and Photophysical Properties of Hexacoordinated Organosilicon Compounds with 2-(2-Pyridyl)phenyl Groups Invited Reviewed International journal

    Furuta, S.; Mori, T.; Yoshigoe, Y.; Sekine, K.; Kuninobu, Y.*

    Org. Biomol. Chem.   18   3239 - 3242   2020.3

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    DOI: 10.1039/D0OB00484G

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  • Synthesis of six-membered silacycles by borane-catalyzed double sila-Friedel–Crafts reaction Invited Reviewed International journal

    Dong, Y.; Sakai, M.; Fuji, K.; Sekine, K.; Kuninobu, Y.*

    Beilstein J. Org. Chem.   16   409 - 414   2020.3

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    DOI: 10.3762/bjoc.16.39

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  • Copper-Catalyzed Tertiary Alkylative Cyanation for the Synthesis of Cyanated Peptide Building Blocks Reviewed International journal

    Miwa, N.; Tanaka, C.; Ishida, S.; Hirata, G.; Song, J.; Torigoe, T.; Kuninobu, Y.*; Nishikata, T.*

    J. Am. Chem. Soc.   142 ( 4 )   1692 - 1697   2020.1

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    DOI: 10.1021/jacs.9b113497

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  • Donor–Acceptor π-Conjugated Enamines: Functional Group-Compatible Synthesis from Amides and Their Photoabsorption and Photoluminescence Properties Reviewed International journal

    Atsushi Tahara, Ikumi Kitahara, Daichi Sakata, Yoichiro Kuninobu, Hideo Nagashima

    J. Org. Chem.   84 ( 23 )   15236 - 15254   2019.12

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    DOI: 10.1021/acs.joc.9b02267

  • Synthesis of Silafluorene Derivatives from Biphenyls and Dihydrosilanes via Double Sila-Friedel-Crafts Reaction Reviewed International journal

    Dong, Y.; Takata, Y.; Yoshigoe, Y.; Sekine, K.; Kuninobu, Y.

    Chem. Commun.   55 ( 88 )   13303 - 13306   2019.11

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    DOI: 10.1039/c9cc07692a

  • 2-Position-Selective Trifluoromethylthiolation of Six-Membered Heteroaromatic Compounds Reviewed International journal

    Muta, R.; Torigoe, T.; Kuninobu, Y.

    Org. Lett.   21 ( 11 )   4289 - 4292   2019.6

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    DOI: 10.1021/acs.orglett.9b01474

  • Palladium-Catalyzed C–H Heteroarylation of 2,5-Disubstituted Imidazoles Invited Reviewed

    Togo, T.; Sohma, Y.; Kuninobu, Y.; Kanai, M.

    Chem. Pharm. Bull.   67 ( 3 )   196 - 198   2019.3

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    DOI: 10.1248/cpb.c18-00586

  • Hydrogen-Bond-Controlled Formal Meta-Selective C-H Transformations and Regioselective Synthesis of Multisubstituted Aromatic Compounds Reviewed

    Jie Wang, Takeru Torigoe, Yoichiro Kuninobu

    Organic Letters   21 ( 5 )   1342 - 1346   2019.3

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    The meta-selective introduction of functional groups into aromatic substrates was successfully achieved by hydrogen-bond-controlled meta-selective C-H borylation and successive conversion of the boryl group to other functional groups. By this method a wide range of functional groups could be introduced without isolation of the borylated intermediates. The desired meta-functionalized aromatic products were obtained in a one-pot manner even on a gram scale. Regioselective synthesis of multisubstituted aromatic compounds was also achieved.

    DOI: 10.1021/acs.orglett.9b00030

  • Hydrogen-Bond-Controlled Formal Meta-Selective C-H Transformations and Regioselective Synthesis of Multisubstituted Aromatic Compounds Reviewed International journal

    Wang, J.; Torigoe, T.; Kuninobu, Y.

    Org. Lett.   21 ( 5 )   1342 - 1346   2019.3

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    DOI: 10.1021/acs.orglett.9b00030

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  • Palladium-catalyzed C–H heteroarylation of 2,5-disubstituted imidazoles Reviewed

    Takaya Togo, Youhei Sohma, Yoichiro Kuninobu, Motomu Kanai

    Chemical and Pharmaceutical Bulletin   196 - 198   2019.1

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    We developed a palladium-catalyzed C–H N-heteroarylation of N-protected-2,5-disubstituted imidazoles at the C4-position using N-heteroaryl halides as a coupling partner. Intensive reaction condition screening led us to identify fluo-rinated bathophenanthroline 7 as the optimum ligand for the palladium catalyst. This reaction will enhance lead optimization of drug candidates by facilitating the synthesis of hetero-biaryl compounds containing an imidazole ring.

    DOI: 10.1248/cpb.c18-00586

  • Rhenium-catalyzed ortho-alkylation of phenols Reviewed

    Yoichiro Kuninobu, Masaki Yamamoto, Mitsumi Nishi, Tomoyuki Yamamoto, Takashi Matsuki, Masahito Murai, Kazuhiko Takai

    Organic Syntheses   94   2018.6

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    A procedure yielding pure 2-(1-methylnonyl)phenol (1) as a colorless oil is presented. An oven-dried Schlenk flask with a Teflon-coated magnetic stir bar and a reflux condenser with a three-way stopcock is primarily used as paraphernalia. A discussion on ortho-monoalkylated phenol derivatives as important bioactive compounds and functional materials concludes the chapter.

    DOI: 10.1002/0471264229.os094.20

  • Near-Infrared Photoactivatable Oxygenation Catalysts of Amyloid Peptide Reviewed

    Jizhi Ni, Atsuhiko Taniguchi, Shuta Ozawa, Yukiko Hori, Yoichiro Kuninobu, Takashi Saito, Takaomi C. Saido, Taisuke Tomita, Youhei Sohma, Motomu Kanai

    Chem   4 ( 4 )   807 - 820   2018.4

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    Toxic aggregation of amyloid peptide and protein is intimately related to a number of human diseases, including Alzheimer's disease (AD). Here, we developed biocompatible photooxygenation catalyst 9, which can selectively oxygenate and degrade the pathogenic aggregation of AD-related amyloid-β peptide (Aβ) under near-infrared (NIR) light irradiation. On the basis of the structure of a fluorescent Aβ probe, CRANAD-2, a bromine atom was introduced to increase the production of singlet oxygen for photooxygenation. The use of julolidine and perfluoroalkylborate moieties as electron-donor and -acceptor components, respectively, markedly enhanced the photocatalytic activity and reduced phototoxicity. Photooxygenation of aggregated Aβ by 9 under NIR irradiation in the presence of cells attenuated the cytotoxicity of Aβ. The tissue permeability of NIR enabled catalytic photooxygenation of aggregated Aβ under the mouse skin. Moreover, injection of the catalyst to the AD-model mouse brain along with NIR light irradiation led to a significant decrease in the intact Aβ level in the brain. An artificial chemical catalysis that can selectively transform toxic aggregates of peptides and proteins to non-toxic species under physiologic conditions would find therapeutic applications to treat currently- incurable amyloid diseases. Because peptide and protein aggregation generally depends on intermolecular hydrophobic interactions, covalent installation of hydrophilic oxygen atoms from aerobic oxygen to a peptide or protein (i.e., oxygenation) would decrease the aggregative property. Here, we report a biocompatible photooxygenation catalyst that can selectively oxygenate and degrade the pathogenic aggregation of the peptide responsible for Alzheimer's disease (AD) under near-infrared light irradiation. The detoxicating chemical catalysis targeting aggregated amyloid-β peptide proceeded in the AD-model mouse brain. The results obtained in this study are an important step toward using artificial catalysis as a potential therapeutic strategy against amyloid diseases. A biocompatible photooxygenation catalyst that can selectively oxygenate and degrade the pathogenic aggregation of Alzheimer's disease (AD)-related amyloid-β peptide (Aβ) under near-infrared light irradiation has been developed. The catalyst oxygenates Aβ embedded under the skin of a living mouse and diminishes the intact Aβ level in an AD-model mouse brain. The new catalyst is potentially applicable for the treatment of peripheral amyloid diseases and AD.

    DOI: 10.1016/j.chempr.2018.02.008

  • 2-Position-Selective C-H Perfluoroalkylation of Quinoline Derivatives Reviewed

    Takahiro Shirai, Motomu Kanai, Yoichiro Kuninobu

    Organic Letters   20 ( 6 )   1593 - 1596   2018.3

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    We developed 2-position-selective, direct C-H trifluoromethylation, pentafluoroethylation, and heptafluoropropylation of quinoline derivatives. Regioselective transformation was achieved without derivatization of the quinolines. The reaction proceeded at room temperature with high functional group tolerance, even in gram scale. Notably, the reaction was applicable to substrates containing a functional group sensitive to oxidation and a drug molecule.

    DOI: 10.1021/acs.orglett.8b00339

  • Preparation of solid-state luminescent materials by complexation between π-conjugated molecules and activators Reviewed

    Takeshi Yamakawa, Yusuke Yoshigoe, Zijia Wang, Motomu Kanai, Yoichiro Kuninobu

    Chemistry Letters   47 ( 11 )   1391 - 1394   2018.1

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    A combination of simple π-conjugated molecules bearing a lone pair on heteroatom(s) and activators afforded new solidstate fluorescent materials. A solid-state red-emitting material that exhibits aggregation-induced emission was also synthesized by the present method.

    DOI: 10.1246/cl.180735

  • Preparation of solid-state luminescent materials by complexation between π-conjugated molecules and activators Reviewed

    Takeshi Yamakawa, Yusuke Yoshigoe, Zijia Wang, Motomu Kanai, Yoichiro Kuninobu

    Chemistry Letters   47 ( 11 )   1391 - 1394   2018.1

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    A combination of simple π-conjugated molecules bearing a lone pair on heteroatom(s) and activators afforded new solidstate fluorescent materials. A solid-state red-emitting material that exhibits aggregation-induced emission was also synthesized by the present method.

    DOI: 10.1246/cl.180735

  • Development of Novel C-H Bond Transformations and Their Application to the Synthesis of Organic Functional Molecules Reviewed

    Yoichiro Kuninobu

    Synlett   29 ( 16 )   2093 - 2107   2018.1

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    This personal account summarizes our recent progress in the development of C-H transformations. We achieved ortho -selective C-H borylations and silylations by using Lewis acid-base interaction between two substrates and we achieved meta - and ortho -selective C-H borylations by using hydrogen bonding or Lewis acid-base interaction between a hydrogen donor or Lewis acid unit of a ligand and a functional group of a substrate. Regioselective C-H trifluoromethylations and related reactions of six-membered heteroaromatic compounds were realized at their 2- and 4-positions and at their benzylic positions. In addition, we developed C-H transformations directed towards the synthesis of organic functional materials, such as highly soluble polyimides or π-conjugated molecules containing either heteroatom(s) or a Lewis acid-base interaction. 1 Introduction 2 Regioselective C-H Transformations Controlled by Noncovalent Bond Interactions 2.1 Regioselective C-H Transformations Controlled by Lewis Acid-Base Interaction between Two Substrates 2.2 Regioselective C-H Transformation Controlled by Hydrogen Bonding between Ligand and Substrate 2.3 Regioselective C-H Transformations Controlled by Lewis Acid-Base Interactions between Ligands and Substrates 3 Trifluoromethylation and Related Transformations of Six-Membered Heteroaromatic Compounds 3.1 2-Position-Selective C-H Trifluoromethylation of Six-Membered Heteroaromatic Compounds 3.2 4-Position-Selective C-H Trifluoromethylation of Six-Membered Heteroaromatic Compounds 3.3 Benzyl Position-Selective C-H Trifluoromethylation of Six-Membered Heteroaromatic Compounds 4 C-H Transformations Leading to the Synthesis of Organic Functional Materials 4.1 Heteroatom-Containing π-Conjugated Molecules 4.2 π-Conjugated Molecules Containing a Lewis Acid-Base Interaction 4.3 Soluble Polyimide Derivatives 5 Conclusions.

    DOI: 10.1055/s-0037-1610531

  • Iridium/Bipyridine-Catalyzed ortho-Selective C-H Borylation of Phenol and Aniline Derivatives Reviewed

    Hong Liang Li, Motomu Kanai, Yoichiro Kuninobu

    Organic Letters   19 ( 21 )   5944 - 5947   2017.11

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    An iridium-catalyzed ortho-selective C-H borylation of phenol and aniline derivatives has been successfully developed. Iridium/bipyridine-catalyzed C-H borylation generally occurred at the meta- and para-positions of aromatic substrates. Introduction of an electron-withdrawing substituent on the bipyridine-type ligand and a methylthiomethyl group on the hydroxy and amino groups of the phenol and aniline substrates, however, dramatically altered the regioselectivity, affording exclusively ortho-borylated products. The reaction proceeded in good to excellent yields with good functional group tolerance. C-H borylation was applied to the synthesis of a calcium receptor modulator.

    DOI: 10.1021/acs.orglett.7b02936

  • Iron-Catalyzed ortho-Selective C−H Borylation of 2-Phenylpyridines and Their Analogs Reviewed International journal

    Yoshigoe, Y.; Kuninobu, Y.

    Org. Lett.   19 ( 13 )   3450 - 3453   2017.6

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    DOI: 10.1021/acs.orglett.7b01423

  • Iron-Catalyzed Acyloxyalkylation of Styrenes Using Hypervalent Iodine Reagents Reviewed International journal

    @Wang, Z.; @Kanai, M.; Kuninobu, Y.

    Org. Lett.   19 ( 9 )   2398 - 2401   2017.4

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    DOI: 10.1021/acs.orglett.7b00923

  • Rhenium-Catalyzed Synthesis of 1,3-Diiminoisoindolines via Insertion of Carbodiimides into a C-H Bond of Aromatic and Heteroaromatic Imidates Reviewed

    Zijia Wang, Shunsuke Sueki, Motomu Kanai, Yoichiro Kuninobu

    Organic Letters   18 ( 10 )   2459 - 2462   2016.5

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    The rhenium-catalyzed synthesis of 1,3-diiminoisoindolines and their related compounds from aromatic or heteroaromatic imidates and carbodiimides are reported via C-H bond activation. This reaction is the first example of a transition-metal-catalyzed insertion of carbodiimides into an aromatic or heteroaromatic C-H bond and a novel method for synthesizing 1,3-diiminoisoindolines and their related compounds. Unsymmetrical 1,3-diiminoisoindolines were easily obtained using this method. The reaction proceeded in good to excellent yield using a variety of substrates.

    DOI: 10.1021/acs.orglett.6b01012

  • Rhodium-Catalyzed Synthesis of Chiral Spiro-9-silabifluorenes by Dehydrogenative Silylation Mechanistic Insights into the Construction of Tetraorganosilicon Stereocenters Reviewed

    Masahito Murai, Yutaro Takeuchi, Kanae Yamauchi, Yoichiro Kuninobu, Kazuhiko Takai

    Chemistry - A European Journal   22 ( 17 )   6048 - 6058   2016.4

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    Mechanistic insight into the construction of quaternary silicon chiral centers by rhodium-catalyzed synthesis of spiro-9-silabifluorenes through dehydrogenative silylation is reported. The C2-symmetric bisphosphine ligand, BINAP, was effective in controlling enantioselectivity, and axially chiral spiro-9-silabifluorenes were obtained in excellent yields with high enantiomeric excess. Monitoring of the reaction revealed the presence of a monohydrosilane intermediate as a mixture of two constitutional isomers. The reaction proceeded through two consecutive dehydrogenative silylations, and the absolute configuration was determined in the first silylative cyclization. Competitive reactions with electron-rich and electron-deficient dihydrosilanes indicated that the rate of silylative cyclization increased with decreasing electron density on the silicon atom of the starting dihydrosilane. Further investigation disclosed a rare interconversion between the two constitutional isomers of the monohydrosilane intermediate with retention of the absolute configuration. Silicon-centered chirality: A combination of [{RhCl(cod)}2] (cod=1,5-cyclooctadiene) and chiral bisphosphine ligand, (R)-BINAP, catalyzes the asymmetric induction of axial chirality through two consecutive dehydrogenative silylations of unactivated C(sp2)-H bonds (see scheme). A mechanistic investigation revealed that the absolute configuration is determined in the first dehydrogenative silylation, and this reaction may involve a rare example of C-Si bond cleavage with retention of the silicon-centered chirality.

    DOI: 10.1002/chem.201504718

  • The development of novel C-H bond transformations and their application to the synthesis of organic functional molecules Reviewed

    Yoichiro Kuninobu

    Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry   74 ( 11 )   1058 - 1068   2016.1

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    This personal account summarizes our recent progress in the development of C-H transformations. We achieved ortho -selective C-H borylation and silylation using Lewis acid-base interaction between two substrates, and meta -selective C-H borylation using hydrogen bonding between a hydrogen donor unit of a ligand and a substrate functional group. Regioselective C-H trifluoromethylation and related reactions of 6-membered heteroaromatic compounds were realized at the 2-, 4-, and benzylic-positions of the heteroaromatic rings. In addition, we developed C-H transformations directed towards the synthesis of organic functional materials, such as highly soluble polyimides and π-conjugated molecules containing either heteroatom(s) or a Lewis acid-base interaction.

    DOI: 10.5059/yukigoseikyokaishi.74.1058

  • Manganese- and Borane-Mediated Synthesis of Isobenzofuranones from Aromatic Esters and Oxiranes via C-H Bond Activation Reviewed

    Shunsuke Sueki, Zijia Wang, Yoichiro Kuninobu

    Organic Letters   18 ( 2 )   304 - 307   2016.1

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    A manganese- and borane-mediated synthesis of isobenzofuranones from esters and oxiranes is developed. The reaction proceeded at aromatic, heteroaromatic, and olefinic C-H bonds with high functional group tolerance. This is the first example of a manganese-catalyzed C-H transformation using an oxygen-directing group. Triphenylborane played an important role in this reaction to cooperatively promote the annulation reaction. Kinetic isotope effect experiments revealed that C-H bond activation of the aromatic rings was the rate-determining step.

    DOI: 10.1021/acs.orglett.5b03474

  • 5-Position-selective C-H trifluoromethylation of 8-aminoquinoline derivatives Reviewed

    Yoichiro Kuninobu, Mitsumi Nishi, Motomu Kanai

    Organic and Biomolecular Chemistry   14 ( 34 )   8092 - 8100   2016.1

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    We developed a copper-catalyzed 5-position-selective C-H trifluoromethylation of 8-aminoquinoline derivatives. The reaction proceeded with high functional group tolerance under mild conditions. In the case of quinolines with an amide, carbamate, urea, or sulfonamide group at the 8-position of quinoline moieties, a radical scavenger experiment indicated that the reaction proceeded via a radical pathway. The protecting group of an 8-amidoquinoline derivative could be removed by hydrolysis. On the other hand, the trifluoromethylation of 8-aminoquinolines was also promoted by other Lewis acids as well as a copper catalyst and proceeded even in the presence of a radical scavenger. These results indicated that the trifluoromethylation of 8-aminoquinolines proceeded via a Friedel-Crafts-type reaction. Interestingly, the copper salt works as either a catalyst for the formation of a CF3 radical or a Lewis acid to promote a Friedel-Crafts-type reaction, depending on the substrate.

    DOI: 10.1039/c6ob01325b

  • C-H Bond Transformations Leading to the Synthesis of Organic Functional Materials Reviewed

    Yoichiro Kuninobu, Shunsuke Sueki

    Synthesis (Germany)   47 ( 24 )   3823 - 3845   2015.12

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    In this review, transition-metal-catalyzed or -mediated C-H transformations leading to the synthesis of organic functional materials, such as oligomers, polymers, and π-conjugated molecules, are summarized. 1 Introduction 2 Oligomers and Polymers 2.1 Synthesis of Oligomers and Polymers 2.2 Chemical Modification of Polymers 3 π-Conjugated Molecules 3.1 Indenes and Fluorenes 3.2 Acenes 3.3 Triphenylenes 3.4 Chemical Modification of Perylene Diimides 3.5 Nanographenes 3.6 Condensed Polycyclic π-Conjugated Molecules with Five-Membered Heteroaromatic Rings 3.7 π-Conjugated Molecules with Nitrogen-Containing Six-Membered Heteroaromatics 3.8 Porphyrins 3.9 Miscellaneous (π-Conjugated Molecules) 4 Miscellaneous (Excluding Polymers and π-Conjugated Molecules) 5 Outlook and Conclusions.

    DOI: 10.1055/s-0035-1560346

  • Acceleration effects of phosphine ligands on the rhodium-catalyzed dehydrogenative silylation and germylation of unactivated C(sp3)-H bonds Reviewed

    Masahito Murai, Hirotaka Takeshima, Haruka Morita, Yoichiro Kuninobu, Kazuhiko Takai

    Journal of Organic Chemistry   80 ( 11 )   5407 - 5414   2015.6

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    The current work describes the marked rate of acceleration caused by phosphine ligands on the rhodium-catalyzed dehydrogenative silylation and germylation of unactivated C(sp3)-H bonds. The reactivity was affected by the steric and electronic nature of the phosphine ligands. The use of the bulky and electron-rich diphosphine ligand (R)-DTBM-SEGPHOS was highly effective to yield the dehydrogenative silylation products selectively in the presence of a hydrogen acceptor. An appropriate choice of C2-symmetric chiral diphosphine ligand enables the asymmetric dehydrogenative silylation via the enantioselective desymmetrization of the C(sp3)-H bond. The unprecedented catalytic germylation of C(sp3)-H bonds with dehydrogenation was also examined with the combination of the rhodium complex and a wide bite angle diphosphine ligand to provide the corresponding 2,3-dihydrobenzo[b]germoles in good yield.

    DOI: 10.1021/acs.joc.5b00920

  • Palladium-catalyzed construction of heteroatom-containing π-conjugated systems by intramolecular oxidative C-H/C-H coupling reaction Reviewed

    Kenta Saito, Prasanna Kumara Chikkade, Motomu Kanai, Yoichiro Kuninobu

    Chemistry - A European Journal   21 ( 23 )   8365 - 8368   2015.6

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    Synthesis of heteroatom-containing ladder-type π-conjugated molecules was successfully achieved via a palladium-catalyzed intramolecular oxidative C-H/C-H cross-coupling reaction. This reaction provides a variety of π-conjugated molecules bearing heteroatoms, such as nitrogen, oxygen, phosphorus, and sulfur atoms, and a carbonyl group. The π-conjugated molecules were synthesized efficiently, even in gram scale, and larger π-conjugated molecules were also obtained by a double C-H/C-H cross-coupling reaction and successive oxidative cycloaromatization.

    DOI: 10.1002/chem.201501116

  • Copper-catalyzed intermolecular C(sp3)-H bond functionalization towards the synthesis of tertiary carbamates Reviewed

    Prasanna Kumara Chikkade, Yoichiro Kuninobu, Motomu Kanai

    Chemical Science   6 ( 5 )   3195 - 3200   2015.5

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    We describe the development of an intermolecular unactivated C(sp3)-H bond functionalization towards the direct synthesis of tertiary carbamates. The transformation proceeded using a readily available, abundant first-row transition metal catalyst (copper), and isocyanates as the source of the amide moiety. This is a novel strategy for direct transformation of a variety of unactivated hydrocarbon feedstocks to N-alkyl-N-aryl and N,N-dialkyl carbamates without pre-functionalization or installation of a directing group. The reaction had a broad substrate scope with 3° > 2° > 1° site selectivity. The reaction proceeded even on a gram scale, and a corresponding free amine was directly obtained when the reaction was performed at high temperature. Kinetic studies suggested that radical-mediated C(sp3)-H bond cleavage was the rate-determining step.

    DOI: 10.1039/c5sc00238a

  • Rhodium-catalysed synthesis of multi-substituted silylindenes from aryl alkynes and hydrosilanes via C-H bond activation Reviewed

    Shunsuke Sueki, Yoichiro Kuninobu

    Chemical Communications   51 ( 36 )   7685 - 7688   2015.5

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    We successfully developed rhodium-catalysed synthesis of multi-substituted silylindenes from 2 equivalents of aryl alkynes and 1 equivalent of hydrosilanes in moderate to good yields via C-H bond activation for the first time. The silyl groups of the obtained silylindenes could be converted to several other functional groups.

    DOI: 10.1039/c5cc01569c

  • Iridium-catalyzed ortho -selective C-H silylation of aromatic compounds directed toward the synthesis of π-conjugated molecules with Lewis acid-base interaction Reviewed

    Takayuki Wakaki, Motomu Kanai, Yoichiro Kuninobu

    Organic Letters   17 ( 7 )   1758 - 1761   2015.4

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    We successfully developed an iridium-catalyzed ortho-selective C-H silylation of aromatic compounds. The reaction exhibited a wide substrate scope, and a variety of π-conjugated molecules were synthesized in good to excellent yields, even in gram scale. Several silyl groups could also be introduced into the products. The experimental results indicated that the regioselectivity could be controlled by a Lewis acid-base interaction between the Lewis acidic silicon atoms of fluorinated hydrosilanes and the Lewis basic nitrogen atoms of aromatic compounds.

    DOI: 10.1021/acs.orglett.5b00529

  • Rhenium-catalysed dehydrogenative borylation of primary and secondary C(sp3)-H bonds adjacent to a nitrogen atom Reviewed

    Masahito Murai, Tetsuya Omura, Yoichiro Kuninobu, Kazuhiko Takai

    Chemical Communications   51 ( 22 )   4583 - 4586   2015.3

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    Rhenium-catalysed C(sp3)-H bond borylation in the absence of any oxidant, hydrogen acceptor, or external ligand, with the generation of H2 as the sole byproduct is described. The transformation, which represents a rare example of rhenium-catalysed C(sp3)-H bond functionalisation, features high atom efficiency and simple reaction conditions. This journal is

    DOI: 10.1039/c4cc09508a

  • Copper-mediated direct C(sp3)-H and C(sp2)-H acetoxylation Reviewed

    Zhen Wang, Yoichiro Kuninobu, Motomu Kanai

    Organic Letters   16 ( 18 )   4790 - 4793   2014.9

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    A copper-mediated terminal position-selective C-(sp3)-H acetoxylation using a bidentate directing group and AgOAc as an oxidant was achieved. This reaction has high functional group tolerance and is not affected by steric hindrance. The reaction proceeds in excellent yield, even in gram scale, and the directing group can be removed after the reaction. Aromatic C(sp2)-H acetoxylation also proceeded under similar reaction conditions.

    DOI: 10.1021/ol5022542

  • Friedel-Crafts functionalization of the cyclopentadienyl ligand in buckymetallocenes Reviewed

    Yutaka Matsuo, Yoichiro Kuninobu, Shingo Ito, Masaya Sawamura, Eiichi Nakamura

    Dalton Transactions   43 ( 20 )   7407 - 7412   2014.5

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    Acylated buckyferrocene and ruthenocene, Fe(η5-C 60Me5)(η5-C5H4COR) (R = Me, Ph, and CHCHPh) and Ru(η5-C60Me 5)(η5-C5H4COR) (R = Me and Ph), were obtained by Friedel-Crafts acylation of the parent buckymetallocenes with the corresponding acid chlorides and aluminum chloride in carbon disulfide at ambient temperature. The electron withdrawing and sterically hindered nature of the acyl groups were revealed by X-ray crystallography, infrared spectroscopy and electrochemical measurements. The possibility of further derivatizing the acylated products was illustrated by the conversion of the acetyl buckyruthenocene into the corresponding hydroxy and acetoxy compounds Ru(η5-C60Me5)(η5-C 5H4CH(OH)Me) and Ru(η5-C 60Me5)(η5-C5H 4CH(OAc)Me). This journal is

    DOI: 10.1039/c3dt52002a

  • Copper-catalyzed benzylic C(sp3)-H alkoxylation of heterocyclic compounds Reviewed

    Noriaki Takemura, Yoichiro Kuninobu, Motomu Kanai

    Organic and Biomolecular Chemistry   12 ( 16 )   2528 - 2532   2014.4

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    We achieved intra- and intermolecular C(sp3)-H alkoxylation of benzylic positions of heteroaromatic compounds using CuBrn (n = 1, 2)/5,6-dimethylphenanthroline (or 4,7-dimethoxyphenanthroline) and ( tBuO)2 as a catalyst and an oxidant, respectively. The reaction proceeded at both terminal and internal benzylic positions of the alkyl groups. The intramolecular alkoxylation was performed on a gram scale. This journal is

    DOI: 10.1039/c4ob00215f

  • Palladium-catalyzed direct C-H silylation and germanylation of benzamides and carboxamides Reviewed

    Kyalo Stephen Kanyiva, Yoichiro Kuninobu, Motomu Kanai

    Organic Letters   16 ( 7 )   1968 - 1971   2014.4

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    A palladium-catalyzed regioselective activation of C(sp2)-H and C(sp3)-H bonds of benzamides and carboxamides, followed by coupling with disilanes to afford organosilanes in moderate to high yields, with the aid of 8-aminoquinoline as a directing group, is reported. Catalytic C(sp 2)-H germanylation of benzamides also proceeds under the same palladium catalysis. The reaction tolerates a wide variety of functional groups and is scalable without yield reduction. The bidentate directing group is readily removed and recovered by the reaction with a hydrazine, with concominant generation of an acyl hydrazide.

    DOI: 10.1021/ol500519y

  • Molybdenum-mediated desulfurization of dhiols and disulfides Reviewed

    Zhen Wang, Yoichiro Kuninobu, Motomu Kanai

    Synlett   25 ( 13 )   1869 - 1872   2014.1

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    We have successfully achieved the molybdenum hexacarbonyl [Mo(CO) 6] mediated desulfurization of thiols and disulfides. In this reaction, the sulfhydryl (SH) mercapto groups of aryl, benzyl, primary and secondary alkyl thiols, and S-S single bonds of disulfides can be removed. This reaction has high functional group tolerance and is not affected by steric hindrance. The results of the reactions in acetone-d 6 suggest that the sources of hydrogen in the thiol and disulfide desulfurizations are the hydrogen atom(s) of a sulfhydryl group and acetone (solvent), respectively, and that the desulfurization proceeds via the formation of an organomolybdenum species.

    DOI: 10.1055/s-0034-1378315

  • Synthesis of pyridine N-oxide-BF2CF3 complexes and their fluorescence properties Reviewed

    Tomoaki Nishida, Aiko Fukazawa, Eriko Yamaguchi, Hiroya Oshima, Shigehiro Yamaguchi, Motomu Kanai, Yoichiro Kuninobu

    Chemistry - An Asian Journal   9 ( 4 )   1026 - 1030   2014

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    Pyridine N-oxide-BF2CF3 and-BF2C 2F5 complexes and their derivatives were synthesized. Most of the complexes show fluorescence both in solution and in the solid state. By expanding the π-conjugated skeleton, the color of the fluorescence could be changed dramatically. A fluorophore with a high solvent dependency could also be produced. Since such compounds can be synthesized on a gram scale in high yield, and are stable to oxygen, water, and heat, the complexes hold great potential as organic functional materials. Too complex for simple answers: Complexes of pyridine N-oxide with BF2CF3 and BF 2C2F5, and their derivatives were synthesized. Most of the complexes fluoresce, both in solution and in the solid state. By expanding the π-conjugated skeleton, the color of the fluorescence could be changed dramatically. Owing to their properties such complexes hold potential as organic functional materials.

    DOI: 10.1002/asia.201301688

  • Copper-catalyzed intramolecular N-S bond formation by oxidative dehydrogenative cyclization Reviewed

    Zhen Wang, Yoichiro Kuninobu, Motomu Kanai

    Journal of Organic Chemistry   78 ( 14 )   7337 - 7342   2013.7

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    Copper-catalyzed synthesis of benzo[d]isothiazol-3(2H)-ones and N-acyl-benzothiazetidine by intramolecular dehydrogenative cyclization is described. In this reaction, a new nitrogen-sulfur (N-S) bond is formed by N-H/S-H coupling. The present reaction has high functional group tolerance and gives products in gram scale. This method promotes double cyclization, allowing for synthesis of a drug intermediate.

    DOI: 10.1021/jo401056g

  • Transition metal-catalyzed highly efficient and novel transformations -Development of reactions using group 7 and other transition metal catalysts Reviewed

    Yoichiro Kuninobu

    Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry   71 ( 5 )   425 - 432   2013.7

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    Rhenium and manganese-catalyzed regioselective insertion of unsaturated molecules into aromatic and olefinic C-H bonds have been achieved. In some cases, successive intramolecular nucleophilic cyclization proceeded. We have also succeeded in regioselective insertion of alkynes into a non-strained C-C single bond of 1,3-dicarbonyl compounds using a rhenium or manganese catalyst. In addition, we have succeeded in regio-and stereo-defined cycloaddition reactions. By using a rhodium or palladium catalyst, we have achieved direct and efficient carbon-heteroatom bond formations via C-H bond activation.

    DOI: 10.5059/yukigoseikyokaishi.71.425

  • Copper-catalyzed N- and O-alkylation of amines and phenols using alkylborane reagents Reviewed

    Shunsuke Sueki, Yoichiro Kuninobu

    Organic Letters   15 ( 7 )   1544 - 1547   2013.4

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    By the reaction of amines with alkylborane reagents in the presence of a catalytic amount of copper(II) acetate Cu(OAc)2 and di-tert-butyl peroxide, a cross-coupling reaction proceeded and alkylated amines were obtained in good to excellent yields. Phenols are also applicable for this reaction, and the corresponding alkyl aryl ethers were produced.

    DOI: 10.1021/ol400323z

  • Copper-catalyzed C-H alkoxylation of azoles Reviewed

    Noriaki Takemura, Yoichiro Kuninobu, Motomu Kanai

    Organic Letters   15 ( 4 )   844 - 847   2013.2

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    We achieved copper-catalyzed intramolecular and intermolecular alkoxylation of azoles. This reaction is a rare example of transition-metal-catalyzed C-H alkoxylation of heteroaromatic compounds. In addition, the alkoxylation reaction proceeded well even in gram scale. In most intermolecular alkoxylations, the use of an excess amount of alcohols (in some cases, alcohols are used as a solvent) is indispensable to efficiently promote the alkoxylation reaction, but this alkoxylation reaction proceeded using only 1 equiv of alcohols.

    DOI: 10.1021/ol303533z

  • Rhodium-catalyzed intramolecular silylation of unactivated C(sp 3)-H bonds Reviewed

    Yoichiro Kuninobu, Takahiro Nakahara, Hirotaka Takeshima, Kazuhiko Takai

    Organic Letters   15 ( 2 )   426 - 428   2013.1

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    The treatment of a variety of hydrosilanes, each incorporating a benzylic C(sp3)-H bond, with a rhodium catalyst resulted in intramolecular dehydrogenative silylation. This silylation reaction was found to occur at typically unreactive C(sp3)-H bonds located at terminal positions on alkyl chains. Interestingly, the rhodium catalyst also promoted regioselective silylation at a site internal to an alkyl chain.

    DOI: 10.1021/ol303353m

  • Palladium-catalyzed synthesis of a phosphine oxide with a chiral phosphorus center via C-H phosphination Reviewed

    Yoichiro Kuninobu, Kazuki Origuchi, Kazuhiko Takai

    Heterocycles   85 ( 12 )   3029 - 3034   2012.12

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    A new phosphine oxide with a chiral phosphine center was synthesized from a bis(biphenyl)phosphine oxide by dehydrogenative intramolecular cyclization via P-H and C-H bond activation under palladium catalysis. The absolute configuration of one enantiomer of the phosphine oxide was determined by single crystal X-ray structure analysis. By reducing the phosphine oxide, the corresponding phosphine, which also has a chiral center, was produced. The phosphine compounds could be optically resolved by chiral HPLC column chromatography.

    DOI: 10.3987/COM-12-12595

  • Rhenium-catalyzed regio- and stereoselective synthesis of γ-thio-α,β-unsaturated ketones via insertion of terminal alkynes into the C-S bond Reviewed

    Mitsumi Nishi, Yoichiro Kuninobu, Kazuhiko Takai

    Organic Letters   14 ( 23 )   6116 - 6118   2012.12

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    The reaction of α-thioketones and alkynes in the presence of a rhenium catalyst, [HRe(CO)4]n, gave γ-thio-α, β-unsaturated ketones in excellent yields. The alkynes were inserted into the carbon-sulfur bond of the α-thioketones, and isomerization of a double bond provided the products with high regio- and stereoselectivities. This reaction also proceeded in an intramolecular fashion.

    DOI: 10.1021/ol302810u

  • Erratum Correction to palladium-catalyzed synthesis of dibenzophosphole oxides via intramolecular dehydrogenative cyclization (Journal of Organic Chemistry (2011) 76 (7370-7376) DOI: 10.1021/jo201030j)) Reviewed

    Yoichiro Kuninobu, Takuya Yoshida, Kazuhiko Takai

    Journal of Organic Chemistry   77 ( 20 )   2012.10

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    DOI: 10.1021/jo3021506

  • Development of novel and highly efficient methods to construct carboncarbon bonds using group 7 transition-metal catalysts Reviewed

    Yoichiro Kuninobu, Kazuhiko Takai

    Bulletin of the Chemical Society of Japan   85 ( 6 )   656 - 671   2012.7

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    Rhenium-or manganese-catalyzed transformations based on the cleavage of inactive bonds, such as carbonhydrogen and carboncarbon bonds are discussed. Such transformations are recognized as key methods to realize efficient and powerful reactions. We also reveal novel regio- and/or stereodefined cycloaddition reactions using a rhenium or manganese catalyst. Most of the catalytic activities are typical of rhenium and manganese carbonyl complexes.

    DOI: 10.1246/bcsj.20120015

  • Rhenium-catalyzed regioselective synthesis of multisubstituted pyridines from β-enamino ketones and alkynes via C-C bond cleavage Reviewed

    Shun Ichi Yamamoto, Kana Okamoto, Makiko Murakoso, Yoichiro Kuninobu, Kazuhiko Takai

    Organic Letters   14 ( 12 )   3182 - 3185   2012.6

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    A new method is described for the regioselective synthesis of multisubstituted pyridine derivatives. Treatment of N-acetyl β-enamino ketones with alkynes in the presence of the rhenium catalyst, Re 2(CO) 10, gives multisubstituted pyridines regioselectively. In this reaction, the N-acetyl moieties are important for the selective formation of the multisubstituted pyridines. This reaction proceeds via insertion of alkynes into a carbon-carbon single bond of β-enamino ketones, intramolecular nucleophilic cyclization, and elimination of acetic acid.

    DOI: 10.1021/ol301273j

  • Rhenium-catalyzed allylation of C-H bonds of benzoic and acrylic acids Reviewed

    Yoichiro Kuninobu, Kazuhiro Ohta, Kazuhiko Takai

    Chemical Communications   47 ( 38 )   10791 - 10793   2011.10

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    We have succeeded in the allylation of aromatic and olefinic C-H bonds of benzoic and acrylic acids using a rhenium catalyst, Re2(CO) 10. In this reaction, isomerization of the introduced allyl group to the 1-propenyl group did not occur.

    DOI: 10.1039/c1cc12359a

  • Synthesis of multisubstituted cyclopentadienes from cyclopentenones prepared via catalytic double aldol condensation and nazarov reaction sequence Reviewed

    Yuta Nishina, Tomohiro Tatsuzaki, Ayano Tsubakihara, Yoichiro Kuninobu, Kazuhiko Takai

    Synlett   ( 17 )   2585 - 2589   2011.10

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    The rhenium-catalyzed synthesis of cyclopentenone derivatives via double aldol condensation and successive Nazarov reaction is described. The cyclopentenones were converted to the corresponding cyclopentadienes using organolithium reagents. Cyclopentadienes with four different substituents could be synthesized by stepwise double aldol condensation using a ketone and two types of aldehydes, followed by treatment with an organolithium reagent.

    DOI: 10.1055/s-0030-1260324

  • Indium-catalyzed construction of polycyclic aromatic hydrocarbon skeletons via dehydration Reviewed

    Yoichiro Kuninobu, Tomohiro Tatsuzaki, Takashi Matsuki, Kazuhiko Takai

    Journal of Organic Chemistry   76 ( 17 )   7005 - 7009   2011.9

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    Polycyclic aromatic compounds can be synthesized from 2-benzylic- or 2-allylbenzaldehydes using a catalytic amount of In(III) or Re(I) complexes. By using this method, polycyclic aza-aromatic compounds can also be prepared efficiently. In these reactions, only water is formed as a side product.

    DOI: 10.1021/jo200861s

  • Palladium-catalyzed synthesis of dibenzophosphole oxides via intramolecular dehydrogenative cyclization Reviewed

    Yoichiro Kuninobu, Takuya Yoshida, Kazuhiko Takai

    Journal of Organic Chemistry   76 ( 18 )   7370 - 7376   2011.9

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    Dibenzophosphole oxides were obtained from secondary hydrophosphine oxides with a biphenyl group by dehydrogenation via phosphine-hydrogen and carbon-hydrogen bond cleavage in the presence of a catalytic amount of palladium(II) acetate, Pd(OAc) 2. By using this reaction, a ladder-type dibenzophosphole oxide could also be synthesized by double intramolecular dehydrogenative cyclization.

    DOI: 10.1021/jo201030j

  • Synthesis of meso-substituted tetraarylalkynylporphyrins via rhenium-catalyzed formation of naphthalene units Reviewed

    Ali Samarat, Yoichiro Kuninobu, Kazuhiko Takai

    Synlett   ( 15 )   2177 - 2180   2011.8

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    Rhenium-catalyzed synthesis of naphthalene-substituted aryl bromides or iodides via C-H bond activation, and its use for palladium-catalyzed cross-coupling reactions with tetraethynylporphyrin are described. A series of novel meso-substituted tetraalkynylporphyrins with naphthalene moieties were obtained.

    DOI: 10.1055/s-0030-1261199

  • Rhenium-catalyzed regio- and stereoselective addition of two carbon units to terminal alkynes via carbon-carbon bond cleavage of β-keto sulfones Reviewed

    Yoichiro Kuninobu, Hironori Matsuzaki, Mitsumi Nishi, Kazuhiko Takai

    Organic Letters   13 ( 11 )   2959 - 2961   2011.6

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    Treatment of β-keto sulfones with terminal alkynes gave unsaturated δ-keto sulfones in good to excellent yields under rhenium catalysis. In this reaction, the insertion of the alkynes into the nonstrained carbon-carbon single bond between the α- and β-positions of the β-keto sulfones proceeded smoothly, and (Z)-isomers were produced with high regio- and stereoselectivities.

    DOI: 10.1021/ol2008507

  • Organic reactions catalyzed by rhenium carbonyl complexes Reviewed

    Yoichiro Kuninobu, Kazuhiko Takai

    Chemical Reviews   111 ( 3 )   1938 - 1953   2011.3

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    Rhenium carbonyl complex-catalyzed synthetic organic reactions are discussed. Kusama and Narasaka reported that a rhenium complex, ReBr(CO) 5, which catalytically promotes Friedel-Crafts acylation. Kusama, Iwasawa, and co-workers reported that the rhenium complex ReCl(CO)5 catalyzes tandem cyclization of ω-ω-acetylenic dienol silyl ethers. Farona and Greenlee reported that a mixture of catalytic amounts of ReX(CO) 5 (X = Cl or Br) and EtAlCl2 promotes olefin metathesis of terminal and internal olefins. The rhenium catalyst is found to promote C-H bond activation followed by insertion of an acrylate, intramolecular nucleophilic cyclization, and finally the elimination of aniline to give the cyclopentadiene derivative, which then complexes to the metal. Fuchikami and co-workers reported the reduction of carboxylic acids to alcohols by dihydrogen.

    DOI: 10.1021/cr100241u

  • Rhenium-catalyzed insertion of terminal alkenes into a C(sp2)-H bond and successive transfer hydrogenation Reviewed

    Yoichiro Kuninobu, Takahiro Nakahara, Peng Yu, Kazuhiko Takai

    Journal of Organometallic Chemistry   696 ( 1 )   348 - 351   2011.1

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    Treatment of aromatic aldimines with terminal alkenes in the presence of a rhenium catalyst, [HRe(CO)4]n, gives 2-alkenylbenzylamines in good to excellent yields. This reaction proceeds via the insertion of the alkene into a C-H bond at the ortho-position of the imino group of the aromatic aldimine followed by sequential β-hydride elimination from the formed alkyl rhenium intermediate and then by hydrogenation of the imino group of the aldimine.

    DOI: 10.1016/j.jorganchem.2010.09.064

  • Iron-catalyzed synthesis of glycine derivatives via carbon-nitrogen bond cleavage using diazoacetate Reviewed

    Yoichiro Kuninobu, Mitsumi Nishi, Kazuhiko Takai

    Chemical Communications   46 ( 46 )   8860 - 8862   2010.12

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    Treatment of tertiary amines with diazoacetate in the presence of a catalytic amount of an iron salt, FeCl3, in ethanol gave glycine derivatives. In this reaction, a carbon-nitrogen single bond of the amine was cleaved.

    DOI: 10.1039/c0cc03781h

  • Cross-coupling reactions between C(sp2)-H and C(sp 3)-H bonds via sequential dehydrogenation and C-H insertion Reviewed

    Yoichiro Kuninobu, Daisuke Asanoma, Kazuhiko Takai

    Synlett   ( 19 )   2883 - 2886   2010.11

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    Formal C(sp2)-H and C(sp3)-H cross-coupling reactions were carried out by iridium-catalyzed transfer dehydrogenation of primary alcohols and sequential manganese-catalyzed insertion of the formed aldehydes into a carbon-hydrogen bond of aromatic or olefinic compounds.

    DOI: 10.1055/s-0030-1259040

  • Synthesis of functionalized pentacenes from isobenzofurans derived from C-H bond activation Reviewed

    Yoichiro Kuninobu, Takayuki Seiki, Shunsuke Kanamaru, Yuta Nishina, Kazuhiko Takai

    Organic Letters   12 ( 22 )   5287 - 5289   2010.11

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    The synthesis of unsymmetric functionalized pentacenes from 1,4-anthraquinones and functionalized isobenzofurans, which were prepared by transformation via C-H bond activation, was successfully accomplished. Examples of the synthesis of pentacenes with functional groups at the 5-position are still rare. These obtained functionalized pentacenes are highly soluble in hexane, toluene, and THF.

    DOI: 10.1021/ol102349r

  • Rhenium-catalyzed diastereoselective synthesis of aminoindanes via the insertion of allenes into a C-H bond Reviewed

    Yoichiro Kuninobu, Peng Yu, Kazuhiko Takai

    Organic Letters   12 ( 19 )   4274 - 4276   2010.10

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    Figure Presented. Aminoindane derivatives were synthesized diastereoselectively by the treatment of aromatic imines with allenes in the presence of a catalytic amount of a rhenium complex, [HRe(CO)4] n. The allenes inserted into the aromatic C-H bonds.

    DOI: 10.1021/ol101627x

  • Regioselective functionalization of alkanes by sequential dehydrogenation-hydrozirconation Reviewed

    Yoichiro Kuninobu, Tomonari Ureshino, Shun Ichi Yamamoto, Kazuhiko Takai

    Chemical Communications   46 ( 29 )   5310 - 5312   2010.7

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    We have succeeded in formal regioselective functionalization of alkanes by iridium-catalyzed dehydrogenation, hydrozirconation of the resulting alkenes, and electrophilic reaction of the generated alkylzirconium intermediate.

    DOI: 10.1039/c0cc00243g

  • Rhenium-catalyzed synthesis of indenones by novel dehydrative trimerization of aryl aldehydes via C-H bond activation Reviewed

    Yoichiro Kuninobu, Takashi Matsuki, Kazuhiko Takai

    Organic Letters   12 ( 13 )   2948 - 2950   2010.7

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    By heating aryl aldehydes with catalytic amounts of a rhenium complex, ReBr(CO)5, and N-phenylacetamide in toluene, indenone derivatives are obtained in good to excellent yields. This reaction proceeds via (1) the formation of an isobenzofuran derivative by the insertion of an aldehyde into the C-H bond of another aldehyde (C-H bond activation) and successive intramolecular nucleophilic cyclization, (2) nucleophilic addition of the formed isobenzofuran derivative to the third aldehyde, (3) isomerization, and (4) intramolecular aldol condensation.

    DOI: 10.1021/ol100947p

  • Rhenium-catalyzed regioselective synthesis of phenol derivatives from 1,3-diesters and terminal alkynes Reviewed

    Yoichiro Kuninobu, Takashi Iwanaga, Mitsumi Nishi, Kazuhiko Takai

    Chemistry Letters   39 ( 8 )   894 - 895   2010.7

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    Treatment of malonates without a substituent at the active methylene moiety with terminal alkynes gave salicylates regioselectively. In contrast, when malonates bearing a substituent at the active methylene moiety were used, cyclic β-keto esters were generated regioselectively. Treatment of the formed cyclic β-keto esters with In(OTf)
    3
    gave phenol derivatives via decarboxylation.

    DOI: 10.1246/cl.2010.894

  • Rhenium- and manganese-catalyzed carbon-carbon bond formation using 1,3-dicarbonyl compounds and alkynes Reviewed

    Yoichiro Kuninobu, Atsushi Kawata, Salprima S. Yudha, Hisatsugu Takata, Mitsumi Nishi, Kazuhiko Takai

    Pure and Applied Chemistry   82 ( 7 )   1491 - 1501   2010.7

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    A rhenium complex, [ReBr(CO)3(thf)]2, catalyzed insertion of terminal alkynes into a C-H bond of active methylene sites of 1,3-dicarbonyl compounds. When a catalytic amount of isocyanide or molecular sieves was added to the reaction mixture, the reaction course changed markedly, and insertion of alkynes into a C-C single bond between α- and β-positions of cyclic and acyclic β-keto esters occurred. The formed acyclic δ-keto esters could be converted to 2-pyranones, which were applied to the synthesis of multisubstituted aromatic compounds via the Diels-Alder reaction and successive elimination of carbon dioxide. In the case of the rhenium-catalyzed reactions between terminal alkynes and β-keto esters without substituent at the α-position, tetrasubstituted benzenes were produced regioselectively by two-to-one reaction of the components. The yields of tetrasubstituted benzenes were improved by using a manganese catalyst.

    DOI: 10.1351/PAC-CON-09-09-21

  • Indium-catalyzed synthesis of keto esters from cyclic 1,3-diketones and alcohols and application to the synthesis of seratrodast Reviewed

    Yoichiro Kuninobu, Atsushi Kawata, Taihei Noborio, Syun Ichi Yamamoto, Takashi Matsuki, Kazumi Takata, Kazuhiko Takai

    Chemistry - An Asian Journal   5 ( 4 )   941 - 945   2010.4

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    Esterification reactions from cyclic 1,3-diketones and alcohols are carried out in the presence of several Lewis acids. In particular, indium(III) triflate, In(OTf)3, iron(III) triflate, Fe-(OTf)3, copper(II) triflate, Cu(OTf)2, and silver(I) triflate, AgOTf, show high catalytic activities. These reactions proceed through the carbon-carbon bond cleavage by a retro-aldol reaction and were found to be highly regioselective even in the presence of other functional groups. This type of reaction can also be applied to the preparation of the keto esters during the synthesis of seratrodast, which is an antiasthmatic and eicosanoid antagonist.

    DOI: 10.1002/asia.200900553

  • Rhenium- and manganese-catalyzed synthesis of aromatic compounds from 1,3-dicarbonyl compounds and alkynes Reviewed

    Yoichiro Kuninobu, Mitsumi Nishi, Atsushi Kawata, Hisatsugu Takata, Yumi Hanatani, S. Salprima Yudha, Aya Iwai, Kazuhiko Takai

    Journal of Organic Chemistry   75 ( 2 )   334 - 341   2010.1

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    (Chemical Equation Presented) We have succeeded in the development of three approaches to the synthesis of aromatic compounds from 1,3-dicarbonyl compounds and alkynes. The first approach is a manganese-catalyzed [2+2+2] cycloaddition between 1,3-dicarbonyl compounds, which have no substituents at the active methylene moiety, and terminal alkynes. This reaction proceeds with high regioselectivity when aryl acetylenes are employed as the alkyne component. The second approach is a rhenium- or manganese-catalyzed formal [2+1+2+1] cycloaddition between β-keto esters and two kinds of alkynes. In this reaction, the aromatic compounds are obtained by the following reaction sequence: (1) insertion of the first alkyne into a carbon-carbon single bond of a β-keto ester, (2) formation of 2-pyranones via intramolecular cyclization with the elimination of ethanol, and (3) Diels-Alder reaction between the formed 2-pyranone and the second alkyne. This reaction provides multisubstituted aromatic compounds in a regioselective manner. The third approach is a rheniumcatalyzed formal [2+2+1+1] cycloaddition reaction from two 1,3-diketones and one alkyne. In this reaction, the aromatic skeleton is constructed from three carbons of the first 1,3-diketone, two carbons of the alkyne, and one carbon of the second 1,3-diketone.

    DOI: 10.1021/jo902072q

  • Rhenium-catalyzed addition of -enamino esters to allenes Reviewed

    Yoichiro Kuninobu, Atsuhiro Yamashita, Shun Ichi Yamamoto, Salprima Yudha S., Kazuhiko Takai

    Synlett   ( 18 )   3027 - 3031   2009.12

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    Treatment of β-enamino esters with terminal allenes in the presence of a catalytic amount of a rhenium complex, [ReBr(CO)3(thf)] 2, gave α-alkenylated β-imino or β-enamino esters. In this reaction, a new carbon-carbon bond is formed between the active methylene moiety of the β-enamino esters and the -carbon of the terminal allenes.

    DOI: 10.1055/s-0029-1218281

  • Rhenium- and manganese-catalyzed insertion of alkynes into a carbon-carbon single bond of cyclic and acyclic 1,3-dicarbonyl compounds Reviewed

    Yoichiro Kuninobu, Atsushi Kawata, Mitsumi Nishi, Salprima Yudha S, Jingjin Chen, Kazuhiko Takai

    Chemistry - An Asian Journal   4 ( 9 )   1424 - 1433   2009.9

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    Treatment of alkynes with cyclic and acyclic 1,3-dicarbonyl compounds in the presence of a catalytic amount of a rhenium or manganese complex gives ring-expanded and carbon-chain extension products, respectively. In these reactions, alkynes insert into a non-strained carbon-carbon single bond of 1,3-dicarbonyl compounds. The ring-expansion reaction is also promoted by the addition of 4-Å molecular sieves instead of a catalytic amount of an isocyanide.

    DOI: 10.1002/asia.200900137

  • Rhenium-catalyzed formation of bicyclo[3.3.1]nonene frameworks by a reaction of cyclic β-keto esters with terminal alkynes Reviewed

    Yoichiro Kuninobu, Junya Morita, Mitsumi Nishi, Atsushi Kawata, Kazuhiko Takai

    Organic Letters   11 ( 12 )   2535 - 2537   2009.6

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    Treatment of cyclic βKeto esters with terminal alkynes in the presence of a catalytic amount of a rhenium complex, [ReBr(CO)3(thf)] 2, gave bicyclo[3.3.1]nonene derivatives. The reaction conditions and yields of the bicyclo[3.3.1]nonenes were improved by the sequential use of tetrabutylammonium fluoride (TBAF) after the rhenium-catalyzed reactions.

    DOI: 10.1021/ol900772h

  • Rhenium-catalyzed insertion of nonpolar and polar unsaturated molecules into an olefinic C-H bond Reviewed

    Yoichiro Kuninobu, Yasuo Fujii, Takashi Matsuki, Yuta Nishina, Kazuhiko Takai

    Organic Letters   11 ( 12 )   2711 - 2714   2009.6

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    Treatment of olefins bearing a directing group with α,β- unsaturated carbonyl compounds, alkynes, or aldehydes in the presence of a catalytic amount of a rhenium complex, [ReBr(CO)3(thf)]2 gave γ,δ-unsaturated carbonyl compounds, dienes, and allyl silyl ethers, respectively. This reaction proceeds via C-H bond activation, insertion of unsaturated molecules into the formed rhenium-carbon bond, and then reductive elimination (or transmetalation in the case of aldehydes).

    DOI: 10.1021/ol900962v

  • Manganese-catalyzed construction of tetrasubstituted benzenes from 1,3-dicarbonyl compounds and terminal acetylenes Reviewed

    Yoichiro Kuninobu, Mitsumi Nishi, Salprima S. Yudha, Kazuhiko Takai

    Organic Letters   10 ( 14 )   3009 - 3011   2008.12

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    (Chemical Equation Presented) Treatment of β-keto esters with terminal acetylenes in the presence of a catalytic amount of a manganese complex, MnBr(CO) 5, and molecular sieves, gave multisubstituted aromatic compounds in good to excellent yields. This reaction employs [2 + 2 + 2] cycloaddition of β-keto esters and 2 equiv of terminal acetylenes with dehydration. In the case of a 1,3-diketone, the corresponding acetophenone derivative and its deacylated compound can be synthesized selectively.

    DOI: 10.1021/ol800969h

  • Rhenium-catalyzed synthesis of multisubstituted aromatic compounds via C-C single-bond cleavage Reviewed

    Yoichiro Kuninobu, Hisatsugu Takata, Atsushi Kawata, Kazuhiko Takai

    Organic Letters   10 ( 14 )   3133 - 3135   2008.12

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    (Chemical Equation Presented) A reaction between a β-keto ester and an acetylene in the presence of a rhenium complex, [ReBr(CO)3(thf)] 2, as a catalyst, provided a 2-pyranone derivative in excellent yield via retro-aldol reaction (C-C single bond cleavage). By adding an acetylene-bearing ester group(s) after the formation of 2-pyranones, an aromatization reaction proceeded and multisubstituted aromatic compounds were obtained in good to excellent yields.

    DOI: 10.1021/ol801226t

  • Rhenium- and manganese-catalyzed insertion of acetylenes into β-keto esters Synthesis of 2-pyranones Reviewed

    Yoichiro Kuninobu, Atsushi Kawata, Mitsumi Nishi, Hisatsugu Takata, Kazuhiko Takai

    Chemical Communications   ( 47 )   6360 - 6362   2008.12

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    Rhenium- and manganese-catalyzed reactions between β-keto esters and acetylenes, followed by treatment with tetrabutylammonium fluoride, gave 2-pyranone derivatives regioselectively.

    DOI: 10.1039/b814694b

  • Reactions and mechanistic studies of rhenium-catalyzed insertion of α,β-unsaturated carbonyl compounds into a C-H bond Reviewed

    Yoichiro Kuninobu, Yuta Nishina, Kayo Okaguchi, Makoto Shouho, Kazuhiko Takai

    Bulletin of the Chemical Society of Japan   81 ( 11 )   1393 - 1401   2008.12

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    A rhenium complex, [ReBr(CO)3(thf)]2, catalyzes the insertion of α, β-unsaturated carbonyl compounds into a C-H bond of aromatic compounds having nitrogen-containing directing groups. In this reaction, Re2(CO)10 can also be used as a catalyst. When imines are employed as the aromatic substrates, sequential cyclization proceeds and indene derivatives are obtained in good to excellent yields. This reactivity is in contrast to those of ruthenium and rhodium complexes, which are usually used as catalysts in the insertion reactions of unsaturated molecules into a C-H bond. Investigations on the reaction mechanism indicate that the rhenium catalyst promotes C-H bond activation of aromatic compounds, the insertion of α, β-unsaturated carbonyl compounds into a Re-C bond, and intramolecular nucleophilic cyclization followed by reductive elimination and the elimination of an amine.

    DOI: 10.1246/bcsj.81.1393

  • Rhenium-catalyzed coupling of 2-propynyl alcohols and several nucleophiles via dehydration Reviewed

    Yoichiro Kuninobu, Hirokazu Ueda, Kazuhiko Takai

    Chemistry Letters   37 ( 8 )   878 - 879   2008.8

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    Treatment of 2-propynyl alcohols with several nucleophiles in the presence of a catalytic amount of a rhenium complex, [ReBr(CO)3(thf)] 2, gave coupling products via dehydration. In these reactions, C-C, C-O, and C-S bonds can be constructed under mild conditions.

    DOI: 10.1246/cl.2008.878

  • Manganese-catalyzed synthesis of hydantoin derivatives from terminal alkynes and isocyanates Reviewed

    Yoichiro Kuninobu, Kou Kikuchi, Kazuhiko Takai

    Chemistry Letters   37 ( 7 )   740 - 741   2008.7

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    Hydantoin derivatives were obtained by the reactions of terminal alkynes with isocyanates in the presence of a catalytic amount of a manganese complex, MnBr(CO)5. This reaction also proceeded using a rhenium complex, Re2(CO)10, or an iron complex, Fe(CO)5, as a catalyst.

    DOI: 10.1246/cl.2008.740

  • Synthesis of metal fullerene complexes by the use of fullerene halides Reviewed

    Yutaka Matsuo, Yoichiro Kuninobu, Ayako Muramatsu, Masaya Sawamura, Eiichi Nakamura

    Organometallics   27 ( 14 )   3403 - 3409   2008.7

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    K(C60R5) (1, R = Me, Ph) was generated by deprotonation of C60R5H (2) and allowed to react with N-fluoropyridinium triflate and N-chloro- and N-bromosuccinimide in benzene at 25°C for 10 min to obtain halogenated fullerenes C60R 5X (3a: R = Me, X = F; 3b: R = Me, X = Cl; 3c: R = Me, X = Br; 4a: R = Ph, X = F; 4b: R = Ph, X = Cl, 4c: R = Ph, X = Br) in good yield. The pentamethyl[60]fullerene halides are useful for the synthesis of a variety of η5-fullerene metal complexes. The reaction of the fullerene bromide 3c with the low-valent transition metal complexes Na[Re(CO) 4], Fe(CO)5, Ru3(CO)12, and Na[Co(CO)4] gave Re(η5-C60Me 5)(CO)3 (5), Fe(η5-C60Me 5)Br(CO)2 (6), Ru(η5-C60Me 5)Br(CO)2 (7), and Co(η5-C 60Me5)(CO)2 (8), respectively. The structures of halide 3c and rhenium complex 5 were determined by X-ray crystallography. Electrochemical measurements on 3b and 3c were also performed. The iron complex 6 was converted into Fe(η5-C60Me5)Cp (9), Fe(η5-C60Me5)Me(CO)2 (10), Fe(η5-C60Me5)(CO)2(CCH) (11), and Fe(η5-C60Me5)(CO)2(CCPh) (12), by ligand exchange reactions.

    DOI: 10.1021/om8001262

  • Hydroarylation of acetylenes, acrylates, and isocyanates with heteroaromatic compounds under rhenium catalysis Reviewed

    Yoichiro Kuninobu, Kou Kikuchi, Yukimi Tokunaga, Yuta Nishina, Kazuhiko Takai

    Tetrahedron   64 ( 26 )   5974 - 5981   2008.6

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    With the aid of a directing group, an imine moiety, heteroaromatic compounds add to acetylenes in the presence of a catalytic amount of [ReBr(CO)3(THF)]2 at the adjacent position of the directing group regioselectively to give hydroarylation of the acetylenes in good to excellent yields. Similarly, heteroaromatic compounds react with acrylates and isocyanates to give the corresponding hydroarylation products under rhenium catalysis.

    DOI: 10.1016/j.tet.2008.01.145

  • Rhenium-catalyzed synthesis of indene derivatives via C-H bond activation Reviewed

    Yoichiro Kuninobu, Yuta Nishina, Atsushi Kawata, Makoto Shouho, Kazuhiko Takai

    Pure and Applied Chemistry   80 ( 5 )   1149 - 1154   2008.5

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    Rhenium complex, [ReBr(CO)3(thf)]2-catalyzed reactions between aromatic imines and either acetylenes or α,β- unsaturated carbonyl compounds gave indene derivatives in good to excellent yields. These reactions proceed via C-H bond activation, insertion of acetylenes or α,β-unsaturated carbonyl compounds, intramolecular nucleophilic cyclization, and reductive elimination. Indene derivatives were also obtained from aromatic ketones and α,β-unsaturated carbonyl compounds in the presence of catalytic amounts of the rhenium complex and p-anisidine. Sequential ruthenium-catalyzed hydroamination of aromatic acetylenes with anilines, and rhenium-catalyzed reactions of the formed aromatic ketimines with α,β-unsaturated carbonyl compounds also provided indene derivatives.

    DOI: 10.1351/pac200880051149

  • Copper(I)- And gold(I)-catalyzed synthesis of 2,4-disubstituted quinoline derivatives from N-Aryl-2-propynylamines Reviewed

    Yoichiro Kuninobu, Yuichi Inoue, Kazuhiko Takai

    Chemistry Letters   36 ( 12 )   1422 - 1423   2007.12

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    2,4-Disubstituted quinoline derivatives were obtained from N-aryl-2-propynylamines catalyzed by copper(I) and gold(I) complexes. The quinoline derivatives could also be obtained by the reaction of N-arylaldimines with terminal acetylenes via the formation of N-aryl-2-propynylamines.

    DOI: 10.1246/cl.2007.1422

  • Rhenium-catalyzed hydroamidation of unactivated terminal alkynes Synthesis of (E)-enamides Reviewed

    S. Salprima Yudha, Yoichiro Kuninobu, Kazuhiko Takai

    Organic Letters   9 ( 26 )   5609 - 5611   2007.12

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    Reactions of cyclic amides with unactivated terminal alkynes in the presence of a catalytic amount of a rhenium complex provided (E)-enamides in high regio- and stereoselectivity (E:Z = >99:<1).

    DOI: 10.1021/ol702564e

  • Rhenium-catalyzed [2 + 2] cycloadditions of norbornenes with internal and terminal acetylenes Reviewed

    Yoichiro Kuninobu, Peng Yu, Kazuhiko Takai

    Chemistry Letters   36 ( 9 )   1162 - 1163   2007.9

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    Treatment of norbornenes with internal and terminal acetylenes in the presence of a catalytic amount of [ReBr(CO)3(thf)]2 gave cyclobutene derivatives in good to excellent yields.

    DOI: 10.1246/cl.2007.1162

  • Rearrangement of indene skeletons under mild conditions Reviewed

    Yoichiro Kuninobu, Hirokazu Ueda, Atsushi Kawata, Kazuhiko Takai

    Journal of Organic Chemistry   72 ( 18 )   6749 - 6752   2007.8

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    (Chemical Equation Presented) Isomerization between two isomers of 1,2-disubstituted 3-aminoindenes occurs via the rearrangement of indene frameworks. In contrast to previous rearrangements of indene derivatives, which occur under high-temperature conditions or the irradiation of light, this rearrangement proceeds at room temperature without UV light irradiation. An amino group at the 3-position plays an important role to accelerate the rearrangement under mild conditions.

    DOI: 10.1021/jo070537w

  • Rhenium-catalyzed synthesis of naphthalene derivatives via insertion of aldehydes into a C-H bond Reviewed

    Yoichiro Kuninobu, Yuta Nishina, Kazuhiko Takai

    Tetrahedron   63 ( 35 )   8463 - 8468   2007.8

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    A rhenium complex, [ReBr(CO)3(THF)]2, catalyzed reactions of aromatic ketimines and aldehydes with dienophiles, followed by dehydration, to give naphthalene derivatives in good to excellent yields. This reaction proceeds via C-H bond activation, insertion of an aldehyde, intramolecular nucleophilic cyclization, reductive elimination, elimination of aniline and Diels-Alder reaction. After dehydration, naphthalene derivatives were formed.

    DOI: 10.1016/j.tet.2007.05.083

  • Rhenium-catalyzed amidation of heteroaromatic compounds via C-H bond activation Reviewed

    Yoichiro Kuninobu, Yukimi Tokunaga, Kazuhiko Takai

    Chemistry Letters   36 ( 7 )   872 - 873   2007.7

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    Regioselective insertion of isocyanates into a C-H bond of heteroaromatic compounds took place using a rhenium catalyst, [ReBr(CO) 3(thf)] 2.

    DOI: 10.1246/cl.2007.872

  • Rhenium-catalyzed addition of trimethylsilylacetylene to aldimines Reviewed

    Yoichiro Kuninobu, Yuichi Inoue, Kazuhiko Takai

    Chemistry Letters   35 ( 12 )   1376 - 1377   2006.12

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    A rhenium complex, [ReBr(CO)3(thf)]2, catalyzes reactions of aldimines with trimethylsilylacetylene to give propargylamines in excellent yields. The reactions proceed at room temperature under solvent-free conditions.

    DOI: 10.1246/cl.2006.1376

  • Sequential ruthenium-catalyzed hydroamination and rhenium-catalyzed C-H bond activation leading to indene derivatives Reviewed

    Yoichiro Kuninobu, Yuta Nishina, Kazuhiko Takai

    Organic Letters   8 ( 13 )   2891 - 2893   2006.6

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    Formal [3+2] annulation of arylacetylenes and α,β-unsaturated carbonyl compounds is achieved in a one-pot reaction by successive treatment of the acetylenes with aniline and a catalytic amount of Ru3(CO) 12 and NH4PF6 and C-H bond activation catalyzed by [ReBr(CO)3(thf)]2. The result suggests that the second rhenium-catalyzed indene formation is not disturbed by the first catalyst system.

    DOI: 10.1021/ol0611292

  • Isocyanate acting as a carbonyl precursor Pyridyl group-assisted formation of 4H-pyrido[1,2-a]pyrimidin-4-ones from ketimines and isocyanates Reviewed

    Yoichiro Kuninobu, Shuhei Nishimura, Kazuhiko Takai

    Organic and Biomolecular Chemistry   4 ( 2 )   203 - 205   2006.4

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    By the reactions of ketimines bearing a pyridyl or a picolyl group on a nitrogen atom of the imine moiety with tosylisocyanate, 4H-pyrido[1,2-a] pyrimidin-4-one derivatives could be obtained in quantitative yields. In these reactions, tosylisocyanate acts as a carbonyl precursor. The pyridyl or picolyl group is a key functional group because it is not only the constituent structure of the 4H-pyrido[1,2-a]pyrimidin-4-one framework but also the promoter of the formation of a ketene intermediate.

    DOI: 10.1039/b516916j

  • Rhenium-catalyzed insertion of terminal acetylenes into a C-H bond of active methylene compounds Reviewed

    Yoichiro Kuninobu, Atsushi Kawata, Kazuhiko Takai

    Organic Letters   7 ( 22 )   4823 - 4825   2005.10

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    (Chemical Equation Presented) A rhenium complex, [ReBr(CO) 3(thf)]2, catalyzed the intermolecular reactions of 1,3-dicarbonyl compounds with terminal acetylenes and gave the corresponding alkenyl derivatives in excellent yields. These reactions could apply to an intramolecular version and gave the corresponding cyclic compounds quantitatively.

    DOI: 10.1021/ol0515208

  • Mössbauer spectroscopy of bucky ferrocenes Lattice dynamics and motional anisotropy of the metal atom Reviewed

    Rolfe H. Herber, Israel Nowik, Yutaka Matsuo, Motoki Toganoh, Yoichiro Kuninobu, Eiichi Nakamura

    Inorganic Chemistry   44 ( 16 )   5629 - 5635   2005.8

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    Temperature-dependent 57Fe Mössbauer effect spectroscopy has been used to elucidate the metal atom dynamics in three neutral and two cationic bucky ferrocenes. For the three diamagnetic complexes Fe(C 60H5)Cp (1), Fe(C60Me5)Cp (2), and Fe(C60Ph5)Cp (3), the metal atom motion is anisotropic and the temperature dependence of the mean-square amplitude of vibration of the metal atom at a number of temperatures is reported. The Mössbauer lattice temperatures have been determined and compared to the parent ferrocene (6). The synthesis and X-ray crystal structure of 3 have been determined at 153(2) K, and the 1H and 13C NMR spectra have been recorded. The cationic complexes derived from 2 and 3 show spin-lattice relaxation. The relaxation rate appears insensitive to the nearest-neighbor environment of the metal atom in this pair.

    DOI: 10.1021/ic050251e

  • Molecular orientation and electronic structure of epitaxial bucky ferrocene (Fe(C60(CH3)5)C5H 5) thin films Reviewed

    Toshihiko Kaji, Toshihiro Shimada, Hiroaki Inoue, Yoichiro Kuninobu, Yutaka Matsuo, Eiichi Nakamura, Koichiro Saiki

    Journal of Physical Chemistry B   108 ( 28 )   9914 - 9918   2004.7

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    Single crystalline epitaxial films of bucky ferrocene (Fe(C 60(CH3)5)C5H5), a hybrid molecule of C60 and ferrocene, were grown on MoS2(0001) substrates. By using reflection high-energy electron diffraction (RHEED) amplified by a microchannel plate (MCP), it was found that the lattice constant of the film decreased from 11.3 ± 0.2 Å at 1-2 monolayer (ML) to 10.2 ± 0.2 Å at 3 ML or thicker. Both of the lattice constants were incommensurate with that of the substrate, which indicates a new type of epitaxial growth. Valence electronic structures of the films at each thickness were measured with ultraviolet photoelectron spectroscopy (UPS) and the energy levels of molecular orbitals were identified in relation to the molecular orientation in the epitaxial film.

  • Nickel, palladium, and platinum complexes of η 5- cyclopentadienide C 60R 5 ligands. Kinetic and thermodynamic stabilization effects of the C 60Ph 5 ligand Reviewed

    Yoichiro Kuninobu, Yutaka Matsuo, Motoki Toganoh, Masaya Sawamura, Eiichi Nakamura

    Organometallics   23 ( 13 )   3259 - 3266   2004.6

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    The nickel-, palladium-, and platinum-RFC p complexes η 5-RFC p)(η 3-allylic) (3b, RFC p = C 60R 5, R = Me, allylic = methallyl; 4a, R = Ph, allylic = allyl; 4b, R = Ph, allylic = methallyl), Pd(η 5- RFC p)(η 3-allylic) (7a, R = Me, allylic = allyl; 7b, R = Me, allylic = methallyl; 7c, R = Me, allylic = crotyl; 8a, R = Ph, allylic = allyl; 8b, R = Ph, allylic = methallyl; 8c, R = Ph, allylic = crotyl), and Pt(η 5-RFC p)(η 3-methallyl) (9, R = Me; 10, R = Ph), were synthesized by transmetalation between K(RFC p) (R = Me, Ph) and [Ni(allylic)Br] 2, [Pd(allylic)Cl] 2, or [Pt(methallyl)Cl] 2 in THF at 25 °C for 10 min. The nickel-PhFC p complexes 4a,b are unusually more stable toward molecular oxygen than the corresponding simple nickel cyclopentadienides and survive in air for many hours at elevated temperature. The crystal structures and the electrochemical properties of the palladium complexes suggest that the unusual stability of the PhFC p complexes is due to the kinetic stabilization effect of the five Ph groups surrounding the metal atom and the thermodynamic stabilization effect of the electron-withdrawing fullerene moiety, hence suggesting new opportunities for the synthesis of otherwise unstable organometallic compounds.

    DOI: 10.1021/om0499153

  • Photoinduced change in the Raman spectrum of buckyferrocene ((Fe(C 60(CH3)5)C5H5) Reviewed

    Toshihiro Shimada, Yoshiro Yamamoto, Toshihiko Kaji, Kenji Itaka, Hideomi Koinuma, Yoichiro Kuninobu, Yutaka Matsuo, Eiichi Nakamura, Koichiro Saiki

    Solid State Communications   132 ( 3-4 )   197 - 201   2004.1

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    The Raman spectrum of buckyferrocene (Fe(C60(CH 3)5)C5H5) changes during laser irradiation at 532 nm. A peak at 1465 cm-1 decreases and a new peak at 1452 cm-1 emerges, which resembles the change in the 'pentagonal pinch mode' during the photopolymerization of C60. Photoinduced polymerization is strongly suggested because fragments from the buckyferrocene dimers are observed during the mass spectroscopy of laser desorbed solid samples. The rate constants of the photoinduced change for the powder crystals were determined at various photon intensities, and linearity was observed. The photoinduced change seems to occur extremely fast in densely packed buckyferrocene films fabricated by vacuum deposition.

    DOI: 10.1016/j.ssc.2004.07.046

  • Synthesis and reactivity of bucky ruthenocene Ru(η5-C 60Me5)(η5-C5H5) Reviewed

    Yutaka Matsuo, Yoichiro Kuninobu, Shingo Ito, Eiichi Nakamura

    Chemistry Letters   33 ( 1 )   68 - 69   2004.1

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    Metathetical coupling of an η5-fullerene ruthenium complex Ru(η5-C60Me5)Cl(CO)2 and sodium cyclopentadienide gives a molecular hybrid of ruthenocene and fullerene, Ru(η5-C60Me5)(η5-C 5H5) (bucky ruthenocene), the structure of which was determined by spectroscopic and crystallographic analyses. The molecule shows unique reactivity among known ferrocene and ruthenocene compounds.

    DOI: 10.1246/cl.2004.68

  • Hybrid of ferrocene and fullerene Reviewed

    Masaya Sawamura, Yoichiro Kuninobu, Motoki Toganoh, Yutaka Matsuo, Masahiro Yamanaka, Eiichi Nakamura

    Journal of the American Chemical Society   124 ( 32 )   9354 - 9355   2002.8

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    "Bucky ferrocenes", molecular hybrids of ferrocene and fullerene, have been synthesized in good yield on gram scale by treatment of C60HMe5 or C70HMe3 with [FeCp(CO)2]2 and their structures studied with physical methods including X-ray crystallography.

    DOI: 10.1021/ja026069j

  • Epitaxial growth and electronic structure of a C60 derivative prepared by using a solution spray technique Reviewed

    T. Shimada, H. Nakatani, K. Ueno, A. Koma, Yoichiro Kuninobu, M. Sawamura, E. Nakamura

    Journal of Applied Physics   90 ( 1 )   209 - 212   2001.7

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    We demonstrate and analyze the epitaxial film formation of a molecular material that cannot be evaporated in vacuum due to thermal decomposition. A solution of the material is sprayed onto single crystalline van der Waals surfaces using a pulse valve under controlled vapor pressure of the solvent. Monolayer epitaxial films are obtained and we propose that the growth is mediated by liquid ultrathin films formed on the surface. Molecular arrangement and electronic structure of C60(CH3)5H films are studied by reflection high energy electron diffraction and ultraviolet photoelectron spectroscopy, respectively. The present technique will be useful to study the electronic structure of recently synthesized molecular materials.

    DOI: 10.1063/1.1379052

  • Half-sandwich metallocene embedded in a spherically extended π-conjugate system. Synthesis, structure, and electrochemistry of Rh(η5-C60Me5)(CO)2 Reviewed

    M. Sawamura, Yoichiro Kuninobu, E. Nakamura

    Journal of the American Chemical Society   122 ( 49 )   12407 - 12408   2000.12

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    DOI: 10.1021/ja005564h

  • Synthesis of pentamethyl-monohydro[60]fullerene C60Me5H and its use as cyclopentadienyl-type ligand precursor Reviewed

    Masaya Sawamura, Motoki Toganoh, Yoichiro Kuninobu, Seiichi Kato, Eiichi Nakamura

    Chemistry Letters   ( 3 )   270 - 271   2000.1

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    Pentamethyl-monohydro[60]fullerene C60Me5H has been synthesized through five-fold addition of methyleopper reagent to C60. The anion C60Me5 generated by deprotonation of C60Me5H forms organometallic complexes with K+ and Tl+ ions with stronger metal-carbon interaction than that in the corresponding pentaphenylated ligand C60Ph5 +.

    DOI: 10.1246/cl.2000.270

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Books

  • Handbook of CH-Functionalization

    Yoichiro Kuninobu(Role:Joint author)

    Wiley  2022.10 

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  • Catalyst with Earth-abundant Elements

    Kuninobu, Y.; Sueki, S.; Kaplaneris, N.; Ackermann, L.(Role:Joint author)

    Royal Society of Chemistry  2020.10 

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    Language:English   Book type:Scholarly book

    DOI: 10.1039/9781788012775

    Other Link: https://pubs.rsc.org/en/content/ebook/978-1-78801-118-1

  • 錯体化合物事典

    國信 洋一郎(Role:Joint author)

    朝倉書店  2019.9 

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    Language:Japanese   Book type:Scholarly book

  • ファインケミカルシリーズ「有機フッ素化合物の最新動向」

    國信 洋一郎(Role:Joint author)

    シーエムシー出版  2018.7 

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    Language:Japanese   Book type:Scholarly book

Presentations

  • 有機機能性分子合成を志向した新規炭素-水素結合変換反応の開発 Invited

    國信 洋一郎

    長崎大学工学部講演会  2020.2 

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    Event date: 2020.2

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:長崎大学文教キャンパス   Country:Japan  

  • 有機機能性分子合成を志向した新規炭素-水素結合変換反応の開発 Invited

    國信 洋一郎

    近畿化学協会有機金属部会第4回例会  2020.1 

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    Event date: 2020.1

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:大阪府立大学中百舌鳥キャンパス   Country:Japan  

  • Development of Regioselective C-H Bond Transformations Invited International conference

    Yoichiro Kuninobu

    NCL Pune-One Day Symposium  2020.1 

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    Event date: 2020.1

    Language:English   Presentation type:Oral presentation (invited, special)  

    Venue:NCL Pune   Country:India  

  • Development of Regioselective C-H Bond Transformations Invited International conference

    Yoichiro Kuninobu

    International Conference on Chemistry for Human Development (ICCHD-2020)  2020.1 

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    Event date: 2020.1

    Language:English   Presentation type:Oral presentation (invited, special)  

    Venue:University of Calcutta   Country:India  

  • Development of C-H Bond Transformations Directed Towards the Synthesis of Organic Functional Molecules Invited

    Yoichiro Kuninobu

    東京大学大学院理学系研究科化学専攻講演会  2019.12 

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    Event date: 2019.12

    Language:English   Presentation type:Oral presentation (invited, special)  

    Venue:東京大学大学院理学系研究科   Country:Japan  

  • 非共有結合性相互作用を利用する炭素-水素結合変換反応における位置選択性制御法の開発 Invited

    國信 洋一郎

    統合物質創製化学研究推進機構 第5回国内シンポジウム  2019.11 

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    Event date: 2019.11

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:北海道大学   Country:Japan  

  • 位置選択的なフッ素系官能基化反応の開発 Invited

    國信 洋一郎

    第6回次世代の有機化学・広島シンポジウム  2019.10 

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    Event date: 2019.10

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:広島大学   Country:Japan  

  • 有機機能性分子合成を志向した新規炭素-水素結合変換反応の開発 Invited

    國信 洋一郎

    CRESTxIoLセンタージョイントシンポジウム  2019.7 

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    Event date: 2019.7

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:山口大学工学部   Country:Japan  

  • Hydrogen Bond-Controlled meta-selective C-H Borylation and Its Applications Invited International conference

    Yoichiro Kuninobu

    The 47th NAITO CONFERENCE, “C-H Bond Activation and Transformation”  2019.7 

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    Event date: 2019.7

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:シャトレーゼ ガトーキングダム サッポロ   Country:Japan  

  • 有機機能性分子合成を志向した新規炭素-水素結合変換反応の開発 Invited

    國信 洋一郎

    北海道大学講演会  2019.6 

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    Event date: 2019.6

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:北海道大学薬学部   Country:Japan  

  • 有機機能性分子合成を志向した新規炭素-水素結合変換反応の開発 Invited

    國信 洋一郎

    武蔵野大学講演会  2019.5 

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    Event date: 2019.5

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:武蔵野大学   Country:Japan  

  • Noncovalent Bond-Controlled Regioselective C-H Transformations Invited

    Yoichiro Kuninobu

    Let’s leap! Challenges in Organic Chemistry  2019.4 

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    Event date: 2019.4

    Language:English   Presentation type:Oral presentation (general)  

    Venue:東京大学大学院理学系研究科化学専攻   Country:Japan  

  • 有機機能性分子合成を志向した新規炭素-水素結合変換反応の開発 Invited

    國信 洋一郎

    富山大学講演会  2019.2 

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    Event date: 2019.2

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:富山大学工学部   Country:Japan  

  • 触媒配位子による基質認識を利用する位置選択的なC-H結合変換反応の開発 Invited

    國信 洋一郎

    新学術「ハイブリッド」第2回公開シンポジウム  2019.1 

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    Event date: 2019.1

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:東北大学 理学研究科サイエンスホール   Country:Japan  

  • Noncovalent Bond-Controlled Regioselective C-H Transformations Invited International conference

    Yoichiro Kuninobu

    The 13th International Symposium on Organic Reactions  2018.11 

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    Event date: 2018.11

    Language:English   Presentation type:Oral presentation (general)  

    Venue:Hsinchu, Taiwan   Country:Japan  

  • Noncovalent Bond-Controlled Regioselective C-H Transformations Invited International conference

    Yoichiro Kuninobu

    18th Tateshina Conference  2018.11 

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    Event date: 2018.11

    Language:English  

    Venue:車山高原、スカイパークホテル   Country:Japan  

    We developed an iridium-catalyzed meta-selective C–H borylation of aromatic compounds using a newly designed catalytic system (Graphical Abstract). The bipyridine derived ligand that binds iridium contains a pendant urea moiety. A hydrogen bonding between this urea and a hydrogen-bond acceptor in the substrate places the iridium in close proximity to the meta-C–H bond and thus controls the regioselectivity.
    An iridium/bipyridine-catalyzed ortho-selective C-H borylation of aryl sulfides was also developed. High ortho-selectivity was achieved by a Lewis acid-base interaction between a boryl group of the ligand and a sulfur atom of the substrate.
    I will also discuss the recent developments based on hydrogen bond-controlled meta-selective C-H borylation.

  • Noncovalent Bond-Controlled Regioselective C-H Transformations Invited International conference

    Yoichiro Kuninobu

    ICPAC Langkawi 2018  2018.10 

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    Event date: 2018.10 - 2018.11

    Language:English   Presentation type:Oral presentation (invited, special)  

    Venue:マレーシア、ランカウイ島   Country:Japan  

  • 非共有結合性相互作用を利用する位置選択的なC-H結合変換反応の開発 Invited

    國信 洋一郎

    第5回次世代の有機化学・広島シンポジウム  2018.10 

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    Event date: 2018.10

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:広島大学   Country:Japan  

  • 遷移金属触媒による炭素-水素結合変換反応 Invited

    國信 洋一郎

    第12回触媒道場  2018.9 

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    Event date: 2018.9

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:長崎   Country:Japan  

  • 有機機能性分子合成を志向した新規炭素-水素結合変換反応の開発 Invited

    國信 洋一郎

    愛媛大学第249回応用化学科セミナーミニシンポジウム  2018.8 

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    Event date: 2018.8

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:愛媛大学   Country:Japan  

  • Development of Regioselective C-H Bond Transformations Invited International conference

    Yoichiro Kuninobu

    第2回日本・スペイン有機合成シンポジウム  2018.5 

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    Event date: 2018.5

    Language:English   Presentation type:Oral presentation (invited, special)  

    Venue:京都大学理学部セミナーハウス   Country:Japan  

  • Regioselective C-H Trifluoromethylation of 6-Membered Heteroaromatic Compounds Invited International conference

    Yoichiro Kuninobu

    ICPAC 2018  2018.3 

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    Event date: 2018.3

    Language:English   Presentation type:Oral presentation (invited, special)  

    Venue:カンボジア、シエムリープ   Country:Cambodia  

  • Regioselective C-H Trifluoromethylation of 6-Membered Heteroaromatic Compounds Invited International conference

    Yoichiro Kuninobu

    ICPAC 2018  2018.3 

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    Event date: 2018.3

    Language:English   Presentation type:Oral presentation (general)  

    Venue:カンボジア、シエムリープ   Country:Japan  

  • 有機機能性分子合成を志向した新規炭素-水素結合変換反応の開発 Invited

    國信 洋一郎

    第44回有機典型元素化学討論会  2017.12 

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    Event date: 2017.12

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:東京工業大学大岡山キャンパス   Country:Japan  

  • 有機機能性分子合成を志向した新規炭素-水素結合変換反応の開発 Invited

    國信 洋一郎

    第4回次世代の有機化学・広島シンポジウム  2017.10 

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    Event date: 2017.10

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:広島大学 東広島キャンパス   Country:Japan  

  • Development of C-H Bond Transformations Directed Towards the Synthesis of Organic Functional Molecules Invited International conference

    Yoichiro Kuninobu

    Lecture at Institute of Chemistry, Chinese Academy of Sciences  2017.9 

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    Event date: 2017.9

    Language:English   Presentation type:Oral presentation (invited, special)  

    Venue:Institute of Chemistry, Chinese Academy of Sciences   Country:China  

  • Development of C-H Bond Transformations Directed Towards the Synthesis of Organic Functional Molecules Invited International conference

    Yoichiro Kuninobu

    Lecture at Peking University  2017.9 

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    Event date: 2017.9

    Language:English   Presentation type:Oral presentation (invited, special)  

    Venue:Peking University   Country:China  

  • Development of C-H Bond Transformations Directed Towards the Synthesis of Organic Functional Molecules Invited International conference

    Yoichiro Kuninobu

    Lecture at Tsinghua University  2017.9 

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    Event date: 2017.9

    Language:English   Presentation type:Oral presentation (invited, special)  

    Venue:Tsinghua University   Country:China  

  • 有機機能性分子合成を志向した新規炭素-水素結合変換反応の開発 Invited

    國信 洋一郎

    第29回若手研究者のためのセミナー  2017.8 

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    Event date: 2017.8

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:九州大学伊都キャンパス   Country:Japan  

  • Noncovalent Bond-Controlled Regioselective C-H Borylation Invited International conference

    Yoichiro Kuninobu

    ISPAC 2017  2017.6 

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    Event date: 2017.6 - 2018.6

    Language:English   Presentation type:Oral presentation (invited, special)  

    Venue:ベトナム、ホーチミン   Country:Viet Nam  

  • 位置選択的なトリフルオロメチル化反応の開発 Invited

    國信 洋一郎

    第14回フッ素相模セミナー  2017.6 

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    Event date: 2017.6

    Language:Japanese   Presentation type:Oral presentation (invited, special)  

    Venue:東ソー(株)東京研究所   Country:Japan  

  • 生物活性分子合成を志向した炭素-水素結合変換反応の開発 Invited

    國信 洋一郎

    日本薬学会第137年会  2017.3 

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    Event date: 2017.3 - 2018.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:仙台   Country:Japan  

  • ビアリール化合物とメルドラム酸誘導体からのフルオレン類の合成

    姜 志彦、関根 康平、國信 洋一郎

    第35回若手研究者のためのセミナー  2024.8 

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    Event date: 2024.8

    Language:Japanese  

    Country:Japan  

  • ロジウム触媒によるアルキンのシリル化を基盤とする含ケイ素環状化合物の選択的な合成

    藤和人、関根康平、國信洋一郎

    第50回有機典型元素化学討論会  2024.4 

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    Event date: 2024.4

    Language:Japanese  

    Venue:市民会館おおみや   Country:Japan  

  • N-アリールオキサミン酸を二官能基化剤とするアルキンのカルバモイルアリール化反応

    岳 高帆、呉 迪、塩塚 朗、関根 康平、國信 洋一郎

    日本化学会第104春季年会  2024.3 

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    Event date: 2024.3

    Language:Japanese  

    Venue:日本大学 船橋キャンパス   Country:Japan  

  • 水素結合を用いたナフタレン誘導体の遠隔位での位置選択的C–Hボリル化反応の開発

    吉野 元規、猪股 志帆、國信 洋一郎

    日本化学会第104春季年会  2024.3 

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    Event date: 2024.3

    Language:Japanese  

    Venue:日本大学 船橋キャンパス   Country:Japan  

  • 二重Friedel-Crafts反応による環状ジラジカルジカチオンの合成とその性質

    許 潤杰、國信 洋一郎

    日本化学会第104春季年会  2024.3 

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    Event date: 2024.3

    Language:English  

    Venue:日本大学 船橋キャンパス   Country:Japan  

  • 可視光駆動型カルバモイルアリール化反応を利用した環状イミドの合成

    高 汰佑、呉 迪、関根 康平、國信 洋一郎

    日本化学会第104春季年会  2024.3 

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    Event date: 2024.3

    Language:Japanese  

    Venue:日本大学 船橋キャンパス   Country:Japan  

  • 金触媒を用いたアリールジイン化合物の環化反応による含ケイ素環状化合物の合成

    藤 和人、関根 康平、國信 洋一郎

    日本化学会第104春季年会  2024.3 

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    Event date: 2024.3

    Language:Japanese  

    Venue:日本大学 船橋キャンパス   Country:Japan  

  • N-アリールオキサミン酸の芳香族炭素–窒素結合切断を鍵とするアルケンのカルバモイルアリール化反応

    塩塚 朗、呉 迪、川島 恭平、森 俊文、関根 康平、國信 洋一郎

    日本化学会第104春季年会  2024.3 

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    Event date: 2024.3

    Language:Japanese  

    Country:Japan  

  • 二重Friedel-Crafts反応によるペンローズ階段型環状分子の合成と物性

    姜 志彦、國信 洋一郎

    日本化学会第104春季年会  2024.3 

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    Event date: 2024.3

    Language:Japanese  

    Venue:日本大学 船橋キャンパス   Country:Japan  

  • ロジウム触媒を用いた含ケイ素環状分子合成法の開発

    藤 和人、関根 康平、國信 洋一郎

    第26回ケイ素化学協会シンポジウム  2023.11 

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    Event date: 2023.11

    Language:Japanese  

    Venue:静岡県清水文化会館   Country:Japan  

  • 金触媒による含ケイ素環状化合物の合成

    関根康平、藤和人、國信洋一郎

    第27回ケイ素化学協会シンポジウム  2023.11 

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    Event date: 2023.11

    Language:Japanese  

    Venue:ラフォーレ那須   Country:Japan  

  • 炭素-水素およびケイ素-水素結合変換に基づく含ケイ素π共役系分子の合成 Invited

    國信 洋一郎

    第27回ケイ素化学協会シンポジウム  2023.11 

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    Event date: 2023.11

    Language:Japanese  

    Venue:リゾートホテル ラフォーレ那須   Country:Japan  

  • Hydrogen Bond-controlled Site-selective C-H Borylation of Naphthalene Derivatives at the Remote-position

    吉野 元起、猪股 志帆、國信 洋一郎

    第69回有機金属化学討論会  2023.9 

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    Event date: 2023.9

    Language:Japanese  

    Venue:大阪大学、吹田キャンパス   Country:Japan  

  • ヒドロキシピレンの特性を活かした光駆動型脱アルキルチオ化反応

    関根康平・呉 迪・塩塚 朗・川島恭平・森 俊文・國信洋一郎

    第33回基礎有機化学討論会  2023.9 

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    Event date: 2023.9

    Language:Japanese  

    Country:Japan  

  • Synthesis of Cyclic Compounds and the Diradical Dication Species and Investigation of Their Properties

    Runjie Xu, Yoichiro Kuninobu

    第33回基礎有機化学討論会  2023.9 

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    Event date: 2023.9

    Language:English  

    Country:Japan  

  • 二重Friedel-Crafts反応による新規環状π共役系分子の創製

    姜 志彦、國信 洋一郎

    第33回基礎有機化学討論会  2023.9 

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    Event date: 2023.9

    Language:Japanese  

    Country:Japan  

  • ロジウム触媒によるベンゾシロール誘導体の合成

    藤 和人、関根 康平、國信 洋一郎

    第68回有機金属化学討論会  2023.9 

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    Event date: 2023.9

    Language:Japanese  

    Venue:オンライン   Country:Japan  

  • LLX 型ピンサー配位子を用いるイリジウム触媒による C(sp3)‒H ボリル化

    鳥越 尊、河津 稜平、峯 海吏、國信 洋一郎

    第68回有機金属化学討論会  2023.9 

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    Event date: 2023.9

    Language:Japanese  

    Venue:オンライン   Country:Japan  

  • LLX型PNSiピンサー配位子を用いたイリジウム触媒によるC(sp³)-Hボリル化

    峯 海吏、鳥越 尊、國信 洋一郎

    第59回化学関連支部合同九州大会  2023.7 

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    Event date: 2023.7

    Language:Japanese  

    Venue:第59回化学関連支部合同九州大会   Country:Japan  

  • 光誘起電子移動を鍵とする芳香族第一級アミンの脱アミノ化反応の開発

    土岐 拓未、塩塚 朗、関根 康平、國信 洋一郎

    第59回化学関連支部合同九州大会  2023.7 

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    Event date: 2023.7

    Language:Japanese  

    Venue:北九州国際会議場   Country:Japan  

  • ピリジン環の求核的活性化を経る3位選択的トリフルオロメチル化

    牟田 龍平、鳥越 尊、國信 洋一郎

    第59回化学関連支部合同九州大会  2023.7 

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    Event date: 2023.7

    Language:Japanese  

    Venue:第59回化学関連支部合同九州大会   Country:Japan  

  • Synthesis of Cyclic Compounds and the Diradical Dication Species and Investigation of Their Properties

    Runjie Xu, 國信 洋一郎

    第60回化学関連支部合同九州大会  2023.7 

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    Event date: 2023.7

    Language:English  

    Country:Japan  

  • Bifunctional 1-Hydroxypyrene-Photocatalyst for Hydrodesulfurization via Reductive C(aryl)–S Bond Cleavage International conference

    Di Wu, Akira Shiozuka, Kohei Sekine, Yoichiro Kuninobu

    10th Pacific Synposium on Radical Chemistry (PSRC-10)  2023.6 

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    Event date: 2023.6

    Language:English  

    Country:Japan  

  • Deaminative Borylation and Hydrodeamination of Aromatic Amines via Radical/Radical Ion Intermediates International conference

    Kohei Sekine, Akira Shiozuka, Takumi Toki, Kyohei Kawashima, Toshifumi Mori, Yoichiro Kuninobu

    10th Pacific Synposium on Radical Chemistry (PSRC-10)  2023.6 

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    Event date: 2023.6

    Language:English  

    Country:Japan  

  • ビアリール化合物とメルドラム酸誘導体からのフルオレン類の合成

    姜 志彦、関根 康平、國信 洋一郎

    第33回万有福岡シンポジウム  2023.6 

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    Event date: 2023.6

    Language:Japanese  

    Country:Japan  

  • 紫外光照射によるSelectfluorを用いる2-メチルベンゼンスルホン酸塩誘導体のベンジル位ジフッ素化

    曾 嘉林、鳥越 尊、國信 洋一郎

    2023.3 

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    Event date: 2023.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:東京理科大学野田キャンパス   Country:Japan  

  • ロジウム触媒を用いたアルキンの分子内および分子間ヒドロ官能基化による含ケイ素環状化合物の選択的な合成

    藤 和人、関根 康平、國信 洋一郎

    日本化学会第103春季年会  2023.3 

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    Event date: 2023.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:東京理科大学野田キャンパス   Country:Japan  

  • Photoinduced Hydrodesulfurization of Alkylthio Group-substituted Aromatic Compounds via C(sp2)-S Bond Cleavage

    Di Wu, Akira Shiozuka, Kohei Sekine, Yoichiro Kuninobu

    日本化学会第103春季年会  2023.3 

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    Event date: 2023.3

    Language:English   Presentation type:Oral presentation (general)  

    Venue:東京理科大学野田キャンパス   Country:Japan  

  • Hydrogen Bond-Accelerated Decatungstate-Catalyzed C(sp3)–H Alkylation of 2-Methylphenylboronic Acid Derivatives 日本化学会第103春季年会、K704-2am-03

    Hui Jiang, Takeru Torigoe, Yoichiro Kuninobu

    日本化学会第103春季年会  2023.3 

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    Event date: 2023.3

    Language:English   Presentation type:Oral presentation (general)  

    Venue:東京理科大学野田キャンパス   Country:Japan  

  • ペプチド主鎖N末端アンモニウムとの静電相互作用を利用したデカタングステン酸塩光触媒によるバリン残基の選択的なC(sp3)–Hアルキル化

    宋 済舟、鳥越 尊、國信 洋一郎

    120回有機合成シンポジウム  2022.6 

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    Event date: 2022.6

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:オンライン   Country:Japan  

  • 光誘起電子移動を鍵とする芳香族第一級アミンの炭素–窒素結合切断を伴うボリル化および脱アミノ化反応の開発

    塩塚 朗、関根 康平、土岐 拓未、川島 恭平、森 俊文、國信 洋一郎

    第46回有機電子移動化学討論会  2022.6 

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    Event date: 2022.6

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:オンライン   Country:Japan  

  • 静電相互作用を利用したデカタングステン酸塩光触媒による2-メチルアニリニウム塩の位置選択的C(sp3)-Hアルキル化

    曾 嘉林、鳥越 尊、國信 洋一郎

    第32回万有福岡シンポジウム  2022.6 

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    Event date: 2022.6

    Language:Japanese   Presentation type:Symposium, workshop panel (public)  

    Venue:九州大学伊都キャンパス椎木講堂   Country:Japan  

  • Decatungstate-catalyzed Site-selective C(sp3)–H Alkylation of 2-Methylanilinium Salts Controlled by Noncovalent Interactions

    Jialin Zeng, Takeru Torigoe, Yoichiro Kuninobu

    日本化学会第102春季年会  2022.3 

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    Event date: 2022.3

    Language:English  

    Venue:オンライン   Country:Japan  

  • ビアリール化合物とメルドラム酸誘導体からのフルオレン類の合成

    姜 志彦、関根 康平、國信 洋一郎

    日本化学会第102春季年会  2022.3 

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    Event date: 2022.3

    Language:Japanese  

    Venue:オンライン   Country:Japan  

  • 光誘起電子移動を鍵とする芳香族アミンのC–N結合切断を伴うボリル化反応の開発

    塩塚 朗、関根 康平、國信 洋一郎

    日本化学会第102春季年会  2022.3 

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    Event date: 2022.3

    Language:Japanese  

    Venue:オンライン   Country:Japan  

  • ヒドロシリル基を有するキノリン骨格トリアリールホスフィン配位子を用いたイリジウム触媒によるC¬–Hボリル化

    峯 海吏、鳥越 尊、國信 洋一郎

    日本化学会第102春季年会  2022.3 

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    Event date: 2022.3

    Language:Japanese  

    Venue:オンライン   Country:Japan  

  • 光誘起電子移動を利用した芳香族第一級アミンの脱アミノ化反応の開発

    土岐 拓未、塩塚 朗、関根 康平、國信 洋一郎

    日本化学会第102春季年会  2022.3 

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    Event date: 2022.3

    Language:Japanese  

    Venue:オンライン   Country:Japan  

  • ヒドロシリル基を有するビピリジン配位子を用いたイリジウム触媒によるC(sp3)–Hボリル化

    河津 稜平、鳥越 尊、國信 洋一郎

    日本化学会第102春季年会  2022.3 

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    Event date: 2022.3

    Language:Japanese  

    Venue:オンライン   Country:Japan  

  • 3-Position-selective Trifluoromethylation of Pyridine Rings Using Nucleophilic Activation based on 1,4-Reduction

    Ryuhei Muta, Takeru Torigoe, Yoichiro Kuninobu

    日本化学会第102春季年会  2022.3 

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    Event date: 2022.3

    Language:English  

    Venue:オンライン   Country:Japan  

  • ペプチド主鎖の末端アンモニウム基とデカタングステン酸塩光触媒との相互作用を利用した選択的なバリン残基のC(sp3)–H官能基化

    宋 済舟、鳥越 尊、國信 洋一郎

    日本化学会第102春季年会  2022.3 

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    Event date: 2022.3

    Language:Japanese  

    Venue:オンライン   Country:Japan  

  • ピリジン類の求核的活性化に基づく3位選択的トリフルオロメチル化

    牟田 龍平、鳥越 尊、國信 洋一郎

    第44回フッ素化学討論会  2021.11 

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    Event date: 2021.11

    Language:Japanese  

    Venue:オンライン   Country:Japan  

  • LLX型NNSiピンサー配位子を有するイリジウム触媒を用いたC(sp3)-Hボリル化

    河津 稜平, 鳥越 尊, 國信 洋一郎

    第67回有機金属化学討論会  2021.9 

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    Event date: 2021.9

    Language:Japanese  

    Venue:オンライン   Country:Japan  

  • ケイ素架橋スチルベン合成反応の開発

    藤 和人, 関根 康平, 國信 洋一郎

    第67回有機金属化学討論会  2021.9 

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    Event date: 2021.9

    Language:Japanese  

    Venue:オンライン   Country:Japan  

  • 非共有結合性相互作用を利用したデカタングステン酸塩光触媒によるC(sp3)-H結合アルキル化の位置選択性制御

    曾 嘉林, 鳥越 尊, 國信 洋一郎

    第67回有機金属化学討論会  2021.9 

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    Event date: 2021.9

    Language:Japanese  

    Venue:オンライン   Country:Japan  

  • ロジウム触媒によるケイ素架橋スチルベンの新規合成反応の開発 International conference

    藤 和人, 関根 康平, 國信 洋一郎

    第58回化学関連支部合同九州大会  2021.7 

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    Event date: 2021.7

    Language:Japanese  

    Venue:オンライン   Country:Japan  

  • Regioselective C(sp3)–H Alkylation of Fructopyranose Derivative by 1,6 HAT International conference

    李 艷茹, 宮本 翔太, 鳥越 尊, 國信 洋一郎

    第58回化学関連支部合同九州大会  2021.7 

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    Event date: 2021.7

    Language:English  

    Venue:オンライン   Country:Japan  

  • 二重炭素―炭素結合形成によるフルオレン合成反応の開発 International conference

    姜 志彦, 関根 康平, 國信 洋一郎

    第58回化学関連支部合同九州大会  2021.7 

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    Event date: 2021.7

    Language:Japanese  

    Venue:オンライン   Country:Japan  

  • デカタングステン酸塩光触媒を用いたアニリニウム塩の位置選択的なC(sp3)–H結合官能基化反応 International conference

    曾 嘉林, 鳥越 尊, 國信 洋一郎

    第58回化学関連支部合同九州大会  2021.7 

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    Event date: 2021.7

    Language:Japanese  

    Venue:オンライン   Country:Japan  

  • デカタングステン酸塩光触媒を用いたアミノ酸残基の選択的C(sp3)-Hアルキル化 International conference

    宋 済舟, 鳥越 尊, 國信 洋一郎

    第58回化学関連支部合同九州大会  2021.7 

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    Event date: 2021.7

    Language:Japanese  

    Venue:オンライン   Country:Japan  

  • LLX型NNSiピンサー配位子を用いたC(sp3)–H結合ホウ素化 International conference

    河津 稜平, 鳥越 尊, 國信 洋一郎

    第58回化学関連支部合同九州大会  2021.7 

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    Event date: 2021.7

    Language:Japanese  

    Venue:オンライン   Country:Japan  

  • ロジウム触媒によるケイ素架橋スチルベン類の新規合成反応の開発

    藤 和人、関根 康平、國信 洋一郎

    第118回有機合成シンポジウム  2021.6 

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    Event date: 2021.6

    Language:Japanese  

    Venue:九州大学伊都キャンパス椎木講堂+オンライン   Country:Japan  

  • 二重炭素―炭素結合形成によるフルオレン合成反応の開発

    姜 志彦、関根 康平、國信 洋一郎

    第118回有機合成シンポジウム  2021.6 

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    Event date: 2021.6

    Language:Japanese  

    Venue:九州大学伊都キャンパス椎木講堂+オンライン   Country:Japan  

  • 光エネルギーを利用する不活性なC–N結合切断を伴う芳香族アミンのボリル化反応

    塩塚 朗、関根 康平、國信 洋一郎

    第118回有機合成シンポジウム  2021.6 

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    Event date: 2021.6

    Language:Japanese  

    Venue:九州大学伊都キャンパス椎木講堂   Country:Japan  

  • 2-Position-Selective C-H Trifluoromethylation of Quinoline Derivatives International conference

    Takahiro SHIRAI, Motomu KANAI, Yoichiro KUNINOBU

    ACS Publications Symposium: The Power of Chemical Transformations  2021.5 

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    Event date: 2021.5

    Language:English  

    Venue:Virtual Event   Country:Japan  

  • ロジウム触媒によるケイ素架橋スチルベン類の新規合成反応の開発

    藤 和人、関根 康平、國信 洋一郎

    日本化学会第101春季年会  2021.3 

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    Event date: 2021.3

    Language:Japanese  

    Venue:オンライン   Country:Japan  

  • Regioselective C(sp3)–H Alkylation of Fructopyranose Derivative by 1,6-HAT

    Yanru Li, Shoto Miyamoto, Takeru Torigoe, Yoichiro Kuninobu

    日本化学会第101春季年会  2021.3 

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    Event date: 2021.3

    Language:English  

    Venue:オンライン   Country:Japan  

  • Borane-catalyzed Double C-H Silylation for the Synthesis of Silacyclic Compounds

    Yafang Dong, Kohei Sekine, Yoichiro Kuninobu

    第30回万有福岡シンポジウム  2020.5 

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    Event date: 2020.5

    Language:English  

    Venue:オンライン   Country:Japan  

  • ニッケル触媒を用いた分子内および分子間C-Hシリル化反応の開発

    藤 和人、関根 康平、國信 洋一郎

    日本化学会第100春季年会  2020.3 

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    Event date: 2020.3

    Language:Japanese  

    Venue:東京理科大学野田キャンパス   Country:Japan  

  • ホウ素触媒を用いる二重シラFriedel-Crafts反応による含ケイ素六員環化合物の合成

    酒井 優光、Yafang Dong、藤 和人、関根 康平、國信 洋一郎

    日本化学会第100春季年会  2020.3 

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    Event date: 2020.3

    Language:Japanese  

    Venue:東京理科大学野田キャンパス   Country:Japan  

  • Synthesis of Silepins from Terphenyls and Dihydrosilanes via Double Sila-Friedel-Crafts Reaction

    Yafang Dong, Kohei Sekine, Yoichiro Kuninobu

    日本化学会第100春季年会  2020.3 

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    Event date: 2020.3

    Language:English  

    Venue:東京理科大学野田キャンパス   Country:Japan  

  • 水素結合を利用したイリジウム触媒によるチオアニソール類のオルト位選択的なC-Hボリル化

    曾 嘉林、内藤 森生、鳥越 尊、山中 正浩、國信 洋一郎

    日本化学会第100春季年会  2020.3 

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    Event date: 2020.3

    Language:Japanese  

    Venue:東京理科大学野田キャンパス   Country:Japan  

  • 含窒素六員環芳香族化合物への位置選択的な含フッ素官能基導入反応の開発

    楢山 光司、牟田 龍平、鳥越 尊、國信 洋一郎

    日本化学会第100春季年会  2020.3 

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    Event date: 2020.3

    Language:Japanese  

    Country:Japan  

  • アミノ酸側鎖の位置選択的なC-Hトリフルオロメチル化

    宋 済舟、鳥越 尊、國信 洋一郎

    日本化学会第100春季年会  2020.3 

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    Event date: 2020.3

    Language:Japanese  

    Venue:東京理科大学野田キャンパス   Country:Japan  

  • シクロデキストリンによる包接を利用した鉄触媒による芳香族化合物の位置選択的C-Hトリフルオロメチル化反応の開発

    盧 旭、鳥越 尊、國信 洋一郎

    日本化学会第100春季年会  2020.3 

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    Event date: 2020.3

    Language:Japanese  

    Venue:東京理科大学野田キャンパス   Country:Japan  

  • Manganese-catalyzed C(sp3)-H Bromination

    Kumar Sneh, Takeru Torigoe, Yoichiro Kuninobu

    日本化学会第100春季年会  2020.3 

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    Event date: 2020.3

    Language:Japanese  

    Venue:東京理科大学野田キャンパス   Country:Japan  

  • 2-フェニルピリジン部位を有する六配位ケイ素化合物の合成とその光物性

    森 俊彰、古田 翔平、吉越 裕介、関根 康平、國信 洋一郎

    日本化学会第100春季年会  2020.3 

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    Event date: 2020.3

    Language:Japanese  

    Venue:東京理科大学野田キャンパス   Country:Japan  

  • デカタングステン酸塩光触媒によるC(sp3)-H結合官能基化反応の静電相互作用を用いた位置選択性制御

    曾 嘉林、鳥越 尊、國信 洋一郎

    日本化学会第100春季年会  2020.3 

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    Event date: 2020.3

    Language:Japanese  

    Venue:東京理科大学野田キャンパス   Country:Japan  

  • ホウ素触媒を用いる連続的なC-Hシリル化反応によるシラフルオレンの合成

    関根 康平、Yafang Dong、高田 雄大、吉越 裕介、國信 洋一郎

    統合物質創製化学研究推進機構 第5回国内シンポジウム  2019.11 

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    Event date: 2019.11

    Language:Japanese  

    Venue:北海道大学   Country:Japan  

  • Lewis Acid-Catalyzed Synthesis of Silafluorenes from Biphenyls and Dihydrosilanes via Double Sila-Friedel-Crafts Reaction

    Yafang Dong, Yuta Takata, Kohei Sekine, Yusuke Yoshigoe, Yoichiro Kuninobu

    第23回ケイ素化学協会シンポジウム  2019.11 

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    Event date: 2019.11

    Language:English  

    Venue:宮崎、フェニックス・シーガイア・リゾート   Country:Japan  

  • ルイス酸―塩基相互作用を利用した蛍光色素のマルチカラー発光とポリマー担持による固体発光特性の制御

    森 敏彰、吉越 裕介、國信 洋一郎

    第30回基礎有機化学討論会  2019.9 

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    Event date: 2019.9 - 2019.12

    Language:Japanese  

    Venue:大阪国際交流センター   Country:Japan  

  • ortho-Selective C–H Borylation of Thioanisole Derivatives Using Iridium Catalyst Bearing a Simple Bipyridine-Type Ligand

    Jialin Zeng, Takeru Torigoe, Yoichiro Kuninobu

    第66回有機金属化学討論会  2019.9 

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    Event date: 2019.9

    Language:English  

    Venue:首都大学東京南大沢キャンパス   Country:Japan  

  • Double C-H Silylation for the Synthesis of Silafluorenes by Borane Catalyst

    Yafang Dong, Yuta Takata, Kohei Sekine, Yusuke Yoshigoe, Yoichiro Kuninobu

    第66回有機金属化学討論会  2019.9 

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    Event date: 2019.9

    Language:English  

    Venue:首都大学東京南大沢キャンパス   Country:Japan  

  • 単純なビピリジン系配位子をもつイリジウム触媒による芳香族イオウ化合物のオルト位選択的C-Hボリル化 Invited

    曾 嘉林、鳥越 尊、國信 洋一郎

    第31回若手研究者のためのセミナー  2019.8 

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    Event date: 2019.8

    Language:Japanese  

    Venue:九州大学筑紫キャンパス   Country:Japan  

  • ポリマーを利用する蛍光色素-ルイス酸間での平衡の調整によるマルチカラーおよび白色発光 Invited

    森 敏彰、吉越 裕介、國信 洋一郎

    第31回若手研究者のためのセミナー  2019.8 

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    Event date: 2019.8

    Language:Japanese  

    Venue:九州大学筑紫キャンパス   Country:Japan  

  • 六員環ヘテロ芳香族化合物の2位選択的C–Hトリフルオロメチルチオ化反応の開発 Invited

    牟田 龍平、鳥越 尊、國信 洋一郎

    第31回若手研究者のためのセミナー  2019.8 

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    Event date: 2019.8

    Language:Japanese  

    Country:Japan  

  • ヨウ素化合物をハロゲン結合ドナーとして用いる発光材料の開発

    吉越 裕介、山川 健司、王 子嘉、金井 求、國信 洋一郎

    第22回ヨウ素学会シンポジウム  2019.8 

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    Event date: 2019.8

    Language:Japanese  

    Venue:千葉大学西千葉キャンパス   Country:Japan  

  • Noncovalent Bond-Controlled Regioselective C-H Transformations International conference

    Yoichiro Kuninobu

    OMCOS 20  2019.7 

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    Event date: 2019.7

    Language:English  

    Venue:Heidelberg   Country:Germany  

  • One-pot meta-Selective Functionalizations of Aromatic Compounds Utilizing Iridium-catalyzed C-H Borylated Products International conference

    Jie Wang, Takeru Torigoe, Yoichiro Kuninobu

    第56回化学関連支部合同九州大会・外国人研究者交流 国際シンポジウム  2019.7 

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    Event date: 2019.7

    Language:English   Presentation type:Symposium, workshop panel (public)  

    Venue:北九州国際会議場   Country:Japan  

  • 単純なビピリジン系配位子をもつイリジウム触媒による芳香族イオウ化合物のオルト位選択的C-Hボリル化 International conference

    曾 嘉林、鳥越 尊、國信 洋一郎

    第56回化学関連支部合同九州大会・外国人研究者交流 国際シンポジウム  2019.7 

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    Event date: 2019.7

    Language:Japanese   Presentation type:Symposium, workshop panel (public)  

    Venue:北九州国際会議場   Country:Japan  

  • Hydrogen Bond-Accelerated meta-Selective C-H Borylation of Aromatic Compounds and Expression of Substrate Specificity International conference

    Xu Lu, Yusuke Yoshigoe, Yoichiro Kuninobu

    第56回化学関連支部合同九州大会・外国人研究者交流 国際シンポジウム  2019.7 

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    Event date: 2019.7

    Language:English   Presentation type:Symposium, workshop panel (public)  

    Venue:北九州国際会議場   Country:Japan  

  • 六員環ヘテロ芳香族化合物の2位選択的C–Hトリフルオロメチルチオ化反応の開発 International conference

    牟田 龍平、鳥越 尊、國信 洋一郎

    第56回化学関連支部合同九州大会・外国人研究者交流 国際シンポジウム  2019.7 

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    Event date: 2019.7

    Language:Japanese   Presentation type:Symposium, workshop panel (public)  

    Venue:北九州国際会議場   Country:Japan  

  • ポリマーを利用する蛍光色素ールイス酸間での平衡の調整によるマルチカラーおよび白色発光 International conference

    森 敏彰、吉越 裕介、國信 洋一郎

    第56回化学関連支部合同九州大会・外国人研究者交流 国際シンポジウム  2019.7 

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    Event date: 2019.7

    Language:Japanese   Presentation type:Symposium, workshop panel (public)  

    Venue:北九州国際会議場   Country:Japan  

  • Double C-H Silylation for the Synthesis of Silafluorenes by Borane Catalyst International conference

    Yafang Dong, Yuta Takata, Kohei Sekine, Yusuke Yoshigoe, Yoichiro Kuninobu

    第56回化学関連支部合同九州大会・外国人研究者交流 国際シンポジウム  2019.7 

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    Event date: 2019.7

    Language:English   Presentation type:Symposium, workshop panel (public)  

    Venue:北九州国際会議場   Country:Japan  

  • Hydrogen Bond-Accelerated meta-Selective C-H Borylation of Aromatic Compounds and Expression of Substrate Specificity International conference

    Xu Lu, Yusuke Yoshigoe, @Haruka Ida, @Mitsumi Nishi, @Motomu Kanai, Yoichiro Kuninobu

    第1回ハイブリッド触媒国際シンポジウム  2019.5 

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    Event date: 2019.5

    Language:Japanese   Presentation type:Symposium, workshop panel (public)  

    Venue:東京大学本郷キャンパス   Country:Japan  

  • ポリマーを利用する蛍光色素-ルイス酸間での平衡の調整によるマルチカラーおよび白色発光の制御

    森 敏彰、吉越裕介、國信 洋一郎

    第29回万有福岡シンポジウム  2019.5 

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    Event date: 2019.5

    Language:Japanese   Presentation type:Symposium, workshop panel (public)  

    Venue:九州大学馬出キャンパス   Country:Japan  

  • ベンゾフェノン誘導体とLewis酸の錯形成による蛍光材料の開発とポリマー担持による固体発光特性の評価

    森 敏彰、吉越裕介、國信 洋一郎

    三地区交歓会  2019.5 

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    Event date: 2019.5

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:九州大学馬出キャンパス   Country:Japan  

  • キノリン類に対するC2位選択的なトリフルオロメチル化反応の開発

    @白井孝宏、國信洋一郎、@金井求

    日本薬学会第139年会  2019.3 

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    Event date: 2019.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:千葉、幕張メッセ   Country:Japan  

  • パラジウム触媒を用いた2,5-に置換イミダゾールのアリール化反応の開発

    藤後貴也、相馬洋平、國信洋一郎、金井求

    日本薬学会第139年会  2019.3 

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    Event date: 2019.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:千葉、幕張メッセ   Country:Japan  

  • 水素結合部位をもつ配位子の改良によるメタ位選択的なC-Hボリル化反応の加速および基質特異性の発現

    盧 旭、吉越 裕介、井田 悠、西 光海、金井 求、國信 洋一郎

    日本化学会第99春季年会  2019.3 

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    Event date: 2019.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:甲南大学岡本キャンパス   Country:Japan  

  • 6員環ヘテロ芳香族化合物の位置選択的なC-Hトリフルオロメチルチオ化反応の開発 Invited

    牟田 龍平、鳥越 尊、國信 洋一郎

    日本化学会第99春季年会  2019.3 

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    Event date: 2019.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:甲南大学岡本キャンパス   Country:Japan  

  • 非共有結合性相互作用を利用した蛍光材料の開発

    森 俊彰、吉越 裕介、國信 洋一郎

    日本化学会第99春季年会  2019.3 

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    Event date: 2019.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:甲南大学岡本キャンパス   Country:Japan  

  • ボラン触媒を用いた二重シラFriedel-Crafts反応によるシラフルオレンの合成

    高田 雄大、吉越 裕介、國信 洋一郎

    日本化学会第99春季年会  2019.3 

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    Event date: 2019.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:甲南大学岡本キャンパス   Country:Japan  

  • meta-Selective Functionalizations of Aromatic Compounds via Iridium-catalyzed C-H Borylation

    Jie Wang, Takeru Torigoe, Yoichiro Kuninobu

    日本化学会第99春季年会  2019.3 

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    Event date: 2019.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:甲南大学岡本キャンパス   Country:Japan  

  • 含窒素芳香族化合物の位置選択的なC-Hトリフルオロメチルチオ化反応の開発

    牟田 龍平、鳥越 尊、國信 洋一郎

    第45回有機典型元素化学討論会  2018.12 

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    Event date: 2018.12

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:朱鷺メッセ:新潟コンベンションセンター   Country:Japan  

  • イリジウム触媒によるC-Hボリル化に基づく形式的なメタ位選択的C-H変換

    鳥越 尊、王 杰、國信 洋一郎

    統合物質創製科学研究推進機構 第4回国内シンポジウム  2018.10 

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    Event date: 2018.10

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:九州大学筑紫キャンパス   Country:Japan  

  • メタ位選択的なC-Hボリル化反応における反応の加速と基質特異性の発現

    盧 旭、吉越 裕介、井田 悠、西 光海、金井 求、國信 洋一郎

    統合物質創製科学研究推進機構 第4回国内シンポジウム  2018.10 

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    Event date: 2018.10

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:九州大学筑紫キャンパス   Country:Japan  

  • 非共有結合性相互作用による分極制御を利用したマルチカラー蛍光分子の開発

    森 敏彰、吉越 裕介、山川 健司、金井 求、國信 洋一郎

    統合物質創製科学研究推進機構 第4回国内シンポジウム  2018.10 

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    Event date: 2018.10

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:九州大学筑紫キャンパス   Country:Japan  

  • Formal meta-C-H Functionalizations via Iridium-catalyzed C-H Borylation

    Jie Wang, Takeru Torigoe, Yoichiro Kuninobu

    第65回有機金属化学討論会  2018.9 

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    Event date: 2018.9

    Language:English   Presentation type:Oral presentation (general)  

    Venue:同志社大学今出川キャンパス   Country:Japan  

  • Improvement of Ligands For ⅿeta-Selective C-H Borylation and Their Kinetics

    盧 旭、吉越 裕介、@井田 悠、@西 光海、@金井 求、國信 洋一郎

    第65回有機金属化学討論会  2018.9 

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    Event date: 2018.9

    Language:English   Presentation type:Oral presentation (general)  

    Venue:同志社大学今出川キャンパス   Country:Japan  

  • 非共有結合性相互作用を利用する蛍光性π共役系化合物の分極制御と高機能化 International conference

    森 敏彰、吉越 裕介、@山川 健司、@金井 求、國信 洋一郎

    第55回化学関連支部合同九州大会・外国人研究者交流 国際シンポジウム  2018.6 

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    Event date: 2018.6

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:北九州国際会議場   Country:Japan  

  • 非共有結合性相互作用が引き起こす蛍光性π共役系分子の発光挙動変化

    吉越 裕介、@山川 健司、@金井 求、國信 洋一郎

    第28回万有福岡シンポジウム  2018.5 

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    Event date: 2018.5

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:九州大学馬出キャンパス   Country:Japan  

  • Control of Solid-state Fluorescent Properties of π-Conjugated Molecules by Non-covalent Bonding

    Yusuke Yoshigoe, @Takeshi Yamakawa, @Zijia Wang, @Motomu Kanai, Yoichiro Kuninobu

    The 98th Annual Meeting 2018 of CSJ  2018.3 

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    Event date: 2018.3

    Language:English   Presentation type:Oral presentation (general)  

    Venue:Funabashi campus, Nihon University   Country:Japan  

  • Photo-induced Coloring of ortho-Borylated 2-Phenylpyridines International conference

    Yusuke Yoshigoe, @Yuji Suzaki, @Kohtaro Osakada, Yoichiro Kuninobu

    IRCCS-JST CREST Joint Symposium “Chemical Sciences facing a difficult challenge”  2018.1 

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    Event date: 2018.1

    Language:English   Presentation type:Oral presentation (general)  

    Venue:Chikushi campus, Kyushu University   Country:Japan  

  • ホウ素化2‐フェニルピリジン類の固相相転移とその機構解明

    吉越裕介, @須崎裕司、@小坂田耕太郎、國信 洋一郎

    統合物質創製化学研究推進機構 第3回国内シンポジウム  2017.10 

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    Event date: 2017.10

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:京都大学、宇治キャンパス   Country:Japan  

  • ピコリン酸アミド配位子をもつパラジウム触媒によるアルデヒドと有機ハロゲン化物からのヘテロアリールケトン合成

    @若木貴行、@藤後貴也、@吉留大輔、國信洋一郎、@金井求

    第64回有機金属化学討論会  2017.9 

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    Event date: 2017.9

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:東北大学川内キャンパス   Country:Japan  

  • 安価な鉄塩によって触媒される2-フェニルピリジンのオルト位選択的C-Hホウ素化

    吉越裕介, 國信 洋一郎

    第29回若手研究者のためのセミナー  2017.8 

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    Event date: 2017.8 - 2018.8

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:九州大学、伊都キャンパス   Country:Japan  

  • Noncovalent Bond-Controlled Regioselective C-H Borylation International conference

    Yoichiro Kuninobu, @Haruka Ida, @Hong-Liang Li, @Mitsumi Nishi, @Motomu Kanai

    OMCOS19  2017.6 

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    Event date: 2017.6 - 2018.6

    Language:English   Presentation type:Oral presentation (general)  

    Venue:韓国、済州島   Country:Korea, Republic of  

  • アミロイドβを標的とした近赤外光で活性化可能な酸素化触媒の開発

    @倪 積智, @谷口 敦彦, @小澤 柊太, @堀 由起子, @富田 泰輔, 國信 洋一郎, @相馬 洋平, @金井 求

    日本薬学会第137年会  2017.3 

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    Event date: 2017.3 - 2018.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:仙台   Country:Japan  

  • Aβ凝集阻害剤の創出を支援するC-Hカップリング反応の開発

    @藤後 貴也, @新谷 卓士, @相馬 洋平, 國信 洋一郎, @金井 求

    日本薬学会第137年会  2017.3 

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    Event date: 2017.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:仙台   Country:Japan  

  • パラジウム触媒によるC-H結合活性化を伴うアルデ ヒドとハロゲン化物からのケトン合成

    @若木 貴行, @藤後 貴也, @吉留 大輔, 國信 洋一郎, @金井 求

    日本薬学会第137年会  2017.3 

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    Event date: 2017.3 - 2018.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:仙台   Country:Japan  

  • Iron-Catalyzed Oxyalkylation of Styrenes Using Hypervalent Iodine Reagents

    #Zijia Wang, @Motomu Kanai, Yoichiro Kuninobu

    日本化学会第97春季年会  2017.3 

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    Event date: 2017.3

    Language:English   Presentation type:Oral presentation (general)  

    Venue:慶應義塾大学 日吉キャンパス   Country:Japan  

  • Development of Iron-Catalyzed C-H Borylation of 2-Phenylpyridines and Their Analogues and Optical Properties of The Products

    Yusuke Yoshigoe, Yoichiro Kuninobu

    日本化学会第97春季年会  2017.3 

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    Event date: 2017.3

    Language:English   Presentation type:Oral presentation (general)  

    Venue:慶應義塾大学 日吉キャンパス   Country:Japan  

  • マンガン触媒を用いたC-H 結合活性化反応に関するDFT 計算

    @飯島千景・@坂田健・@末木俊輔・國信洋一郎

    日本化学会第97春季年会  2017.3 

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    Event date: 2017.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Country:Japan  

  • ortho-Selective C-H Borylation of Aromatic Compounds Using Distal Functional Group

    @Hongliang Li, Yoichiro Kuninobu, @Motomu Kanai

    日本化学会第97春季年会  2017.3 

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    Event date: 2017.3

    Language:English   Presentation type:Oral presentation (general)  

    Venue:慶應義塾大学 日吉キャンパス   Country:Japan  

  • イリジウム触媒を用いるピリジン類の4位選択的なC-H ホウ素化

    @山川健司、國信洋一郎、@金井求

    日本化学会第97春季年会  2017.3 

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    Event date: 2017.3

    Language:Japanese   Presentation type:Oral presentation (general)  

    Venue:慶應義塾大学 日吉キャンパス   Country:Japan  

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MISC

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Industrial property rights

Patent   Number of applications: 2   Number of registrations: 1
Utility model   Number of applications: 0   Number of registrations: 0
Design   Number of applications: 0   Number of registrations: 0
Trademark   Number of applications: 0   Number of registrations: 0

Professional Memberships

  • American Chemical Society

  • The Chemical Society of Japan

  • The Society of Synthetic Organic Chemistry, Japan

  • The Pharmaceutical Society of Japan

  • Kinka Chemical Society, Japan

  • The Society of Physical Organic Chemistry, Japan

  • The Society of Silicon Chemistry JAPAN

  • The Society of Fluorine Chemistry, Japan

  • SIS the Society of Iodine Science

  • KINKI CHEMICAL SOCIETY, JAPAN

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  • The Society of Synthetic Organic Chemistry, Japan

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  • THE PHARMACEUTICAL SOCIETY OF JAPAN

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  • The Chemical Society of Japan

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  • THE SOCIETY OF FLUORINE CHEMISTRY, JAPAN

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  • The Society of Physical Organic Chemistry, Japan

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  • The Society of Iodine Science

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  • Society of Silicon Chemistry

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  • American Chemical Society

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Committee Memberships

  • 近畿化学協会有機金属部会   Organizer   Domestic

    2020.1 - 2023.12   

  • ケイ素化学協会   Executive   Domestic

    2020.1 - 2023.12   

  • 近畿化学協会有機金属部会   幹事   Domestic

    2020.1 - 2023.12   

  • ケイ素化学協会   理事   Domestic

    2020.1 - 2023.12   

  • 有機合成化学協会九州山口支部   Organizer   Domestic

    2020.1 - 2020.12   

  • 有機合成化学協会九州山口支部   庶務幹事   Domestic

    2020.1 - 2020.12   

  • 有機合成化学協会九州山口支部   Organizer   Domestic

    2019.1 - 2019.12   

  • 有機合成化学協会九州山口支部   会計幹事   Domestic

    2019.1 - 2019.12   

  • 有機合成化学協会九州山口支部   Organizer   Domestic

    2018.1 - 2018.12   

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Academic Activities

  • Screening of academic papers

    Role(s): Peer review

    2023

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    Type:Peer review 

    Number of peer-reviewed articles in foreign language journals:11

  • Screening of academic papers

    Role(s): Peer review

    2022

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    Type:Peer review 

    Number of peer-reviewed articles in foreign language journals:14

    Number of peer-reviewed articles in Japanese journals:0

    Proceedings of International Conference Number of peer-reviewed papers:0

    Proceedings of domestic conference Number of peer-reviewed papers:0

  • Screening of academic papers

    Role(s): Peer review

    2021

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    Type:Peer review 

    Number of peer-reviewed articles in foreign language journals:30

    Number of peer-reviewed articles in Japanese journals:0

    Proceedings of International Conference Number of peer-reviewed papers:0

    Proceedings of domestic conference Number of peer-reviewed papers:0

  • 世話人

    有機合成化学協会九州山口支部有機合成化学講演会  ( Japan ) 2020.11

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    Type:Competition, symposium, etc. 

  • 実行委員

    ケイ素化学協会シンポジウム  ( Japan ) 2020.11

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    Type:Competition, symposium, etc. 

  • 実行委員

    第117回有機合成シンポジウム  ( Japan ) 2020.10

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    Type:Competition, symposium, etc. 

  • 世話人 International contribution

    第57回化学関連支部合同九州大会  ( Japan ) 2020.6

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    Type:Competition, symposium, etc. 

  • Screening of academic papers

    Role(s): Peer review

    2020

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    Type:Peer review 

    Number of peer-reviewed articles in foreign language journals:39

    Number of peer-reviewed articles in Japanese journals:0

    Proceedings of International Conference Number of peer-reviewed papers:0

    Proceedings of domestic conference Number of peer-reviewed papers:0

  • 共同世話人

    ケイ素化学協会シンポジウム  ( Japan ) 2019.11

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    Type:Competition, symposium, etc. 

  • 世話人

    有機合成化学協会九州山口支部 第31回若手研究者のためのセミナー  ( Japan ) 2019.8

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    Type:Competition, symposium, etc. 

  • 主催者

    第1回機能分子化学若手シンポジウム  ( Japan ) 2019.6

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    Type:Competition, symposium, etc. 

  • 科学技術予測センター 専門調査員

    Role(s): Review, evaluation

    2019.6 - 2022.3

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    Type:Scientific advice/Review 

  • 科学技術予測センター 専門調査員

    2019.6

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  • Co-Organizer

    第29回福岡万有シンポジウム  ( Japan ) 2019.5

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    Type:Competition, symposium, etc. 

  • Screening of academic papers

    Role(s): Peer review

    2019

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    Type:Peer review 

    Number of peer-reviewed articles in foreign language journals:84

    Number of peer-reviewed articles in Japanese journals:0

    Proceedings of International Conference Number of peer-reviewed papers:0

    Proceedings of domestic conference Number of peer-reviewed papers:0

  • 共同世話人

    近畿化学協会有機金属部会平成30年度第3回例会  ( Japan ) 2018.10

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    Type:Competition, symposium, etc. 

  • 事務局長 International contribution

    IRCCS-JST CREST Joint Symposium “Chemical Sciences facing a difficult challenge”  ( Japan ) 2018.1

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    Type:Competition, symposium, etc. 

  • Screening of academic papers

    Role(s): Peer review

    2018

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    Type:Peer review 

    Number of peer-reviewed articles in foreign language journals:70

    Number of peer-reviewed articles in Japanese journals:0

    Proceedings of International Conference Number of peer-reviewed papers:0

    Proceedings of domestic conference Number of peer-reviewed papers:0

  • Screening of academic papers

    Role(s): Peer review

    2017

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    Type:Peer review 

    Number of peer-reviewed articles in foreign language journals:63

    Number of peer-reviewed articles in Japanese journals:0

    Proceedings of International Conference Number of peer-reviewed papers:0

    Proceedings of domestic conference Number of peer-reviewed papers:0

  • Screening of academic papers

    Role(s): Peer review

    2016

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    Type:Peer review 

    Number of peer-reviewed articles in foreign language journals:8

    Number of peer-reviewed articles in Japanese journals:0

    Proceedings of International Conference Number of peer-reviewed papers:0

    Proceedings of domestic conference Number of peer-reviewed papers:0

▼display all

Research Projects

  • Creation of Novel Catalysts and Development of Highly Selective C-H Transformations Focusing on Noncovalent Interactions

    Grant number:24K01489  2024 - 2026

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (B)

    國信 洋一郎

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    Authorship:Principal investigator  Grant type:Scientific research funding

    本研究では、非共有結合性相互作用を利用する独自の触媒を創製することで、位置選択的およびエナンチオ選択的な炭素-水素(C-H)結合変換反応を開発する。この際に、金属触媒とともに、金属触媒では実現の難しいラジカル的なC(sp3)-H結合変換反応を選択的に進行させるため有機触媒についても検討する。また、触媒と基質の置換基との立体反発の利用により、芳香族化合物のパラ位選択的なC-H結合変換反応を達成する。さらに、電荷を有する官能基を導入した触媒とそれとは異なる電荷を有するキラル添加剤の間に働く静電相互作用により光学活性な超分子触媒を創製し、エナンチオ選択的C(sp3)-H結合変換反応も実現する。

    CiNii Research

  • Development of Regio- and Enantioselective Transformations Using Data Science

    Grant number:22H05370  2022 - 2023

    Japan Society for the Promotion of Science・Ministry of Education, Culture, Sports, Science and Technology  Grants-in-Aid for Scientific Research  Grant-in-Aid for Transformative Research Areas (A)

    國信 洋一郎

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    Authorship:Principal investigator  Grant type:Scientific research funding

    本研究では、我々が精力的に研究を行ってきた位置選択的なC-H結合変換反応開発の経験と知見を活かし、触媒と光学活性な添加剤、基質と光学活性な添加剤、触媒と基質、それぞれの間に働く非共有結合性相互作用を利用することで、位置選択的かつエナンチオ選択的なC-H結合変換反応を開発する。反応開発で得られるポジティブおよびネガティブなデータをデータベースに提供し、機械学習により提供される触媒設計指針を実験にフィードバックし、再び触媒の合成と反応について検討する、という一連の作業を繰り返すことで、高い位置選択性やエナンチオ選択性を有するC-H結合変換反応を開発する。

    CiNii Research

  • 有機機能性材料への利用を志向した湾曲π共役系分子の開発

    2022 - 2023

    松籟科学技術振興財団 研究助成

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    Authorship:Principal investigator  Grant type:Contract research

  • Creation of Regio- and Stereocontrol Methods of C-H Transformations

    Grant number:21H01941  2021 - 2023

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (B)

    Kuninobu Yoichiro

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    Authorship:Principal investigator  Grant type:Scientific research funding

    The ortho- and benzyl-position-selective C(sp3)-H alkylation of aromatic anilinium salts has been successfully developed by utilizing the electrostatic interaction between catalyst and substrate. By using this reaction, valine-selective C(sp3)-H alkylation of dipeptides and tripeptides containing valine(s) was realized. We also found that the C(sp2)-H borylation at the 2-position of indole derivatives is greatly accelerated by utilizing hydrogen bonds between the substrate and the additive. Furthermore, by inclusion of aromatic compounds in cyclodextrin, which is a cyclic compound, we succeeded in developing site-selective C(sp2)-H trifluoromethylation of aromatic compounds.

    CiNii Research

  • 湾曲したナノグラフェン類および含ヘテロ原子π共役系分子の創製

    2021 - 2022

    徳山科学技術振興財団 2021年度研究助成

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    Authorship:Principal investigator  Grant type:Contract research

  • 合成・分解再利用が容易な糖・糖鎖ポリマーの合成

    2021

    糖業協会 糖類に関する調査研究活動に対する助成事業

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    Authorship:Principal investigator  Grant type:Contract research

  • 波長変換材料の開発

    2020.4 - 2023.3

    Joint research

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    Authorship:Principal investigator  Grant type:Other funds from industry-academia collaboration

  • 触媒と環状分子とのハイブリッドによる高選択的有機合成反応の開発

    Grant number:20H04824  2020 - 2021

    Japan Society for the Promotion of Science・Ministry of Education, Culture, Sports, Science and Technology  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research on Innovative Areas

    國信 洋一郎

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    Authorship:Principal investigator  Grant type:Scientific research funding

    本研究では、C-H結合変換反応による新たな位置選択性制御法を確立するとともに、位置および立体選択的なC-H結合変換反応を実現するため、以下の2つの課題を検討する:①金属触媒と環状分子の協働利用:環状分子により基質を包接することで、基質の反応性が電子的に向上するとともに、望まない反応点が立体的にブロックされることで位置選択性が制御される;②環状部位をもつ遷移金属触媒もしくは有機触媒の利用:環状部位と基質間の超分子相互作用を利用することで触媒活性部位に反応点が近づき、反応の加速と位置選択性の制御が起こる。本研究では、光学活性触媒の利用による不斉反応の開発や、医薬品分子の短工程合成も検討する。

    CiNii Research

  • 炭素-水素結合変換反応における位置選択性制御法の確立

    2019 - 2020

    山田科学振興財団2019年度研究援助

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    Authorship:Principal investigator  Grant type:Contract research

  • 金属錯体/ホスト分子ハイブリッド触媒系の創製と選択的C-H変換反応の開発

    Grant number:18H04656  2018 - 2019

    Japan Society for the Promotion of Science・Ministry of Education, Culture, Sports, Science and Technology  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research on Innovative Areas

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    Authorship:Principal investigator  Grant type:Scientific research funding

  • 農業施設用部材や太陽電池を志向する高性能波長変換材料の開発

    2018 - 2019

    国立研究開発法人科学技術振興機構 研究成果展開事業 A-STEP機能検証フェーズ

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    Authorship:Principal investigator  Grant type:Contract research

  • 動的共有結合を利用する位置選択的な炭素-水素結合変換反応の開発

    2018 - 2019

    平成30年度三菱財団助成

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    Authorship:Principal investigator  Grant type:Contract research

  • 超分子相互作用を利用する位置選択的フッ素系官能基化反応の開発

    2018 - 2019

    武田科学振興財団ライフサイエンス研究助成

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    Authorship:Principal investigator  Grant type:Contract research

  • π共役系内にLewis酸-塩基相互作用をもつ新規π共役系分子の創製

    2018 - 2019

    2018年度住友財団基礎科学研究助成

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    Authorship:Principal investigator  Grant type:Contract research

  • タンパク質をターゲットとする水系溶媒中での位置選択的な酸化反応の開発

    2018 - 2019

    内藤記念科学振興財団研究助成

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    Authorship:Principal investigator  Grant type:Contract research

  • 固体でも水溶液でも光る蛍光材料の開発

    2018

    2018年度池谷科学振興財団 研究助成

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    Authorship:Principal investigator  Grant type:Contract research

  • ハロゲン結合により機能発現する蛍光性化合物の開発

    2018

    2018年度ヨウ素研究助成

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    Authorship:Principal investigator  Grant type:Contract research

  • 非共有結合性相互作用による炭素-水素結合変換反応の位置選択性制御法の確立

    Grant number:17H03016  2017 - 2019

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (B)

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    Authorship:Principal investigator  Grant type:Scientific research funding

  • 位置選択的なトリフルオロメチル化反応の開発

    Grant number:16K13946  2016 - 2017

    Grants-in-Aid for Scientific Research  Grant-in-Aid for challenging Exploratory Research

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    Authorship:Principal investigator  Grant type:Scientific research funding

  • 医薬品合成を志向するC-Hトリフルオロメチル化反応の開発

    2016 - 2017

    公益財団法人薬学振興会 平成27年度基礎的研究助成

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    Authorship:Principal investigator  Grant type:Contract research

  • 非共有結合性相互作用を利用する炭素-水素結合変換反応の開発

    Grant number:26288014  2014 - 2016

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (B)

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    Authorship:Principal investigator  Grant type:Scientific research funding

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Educational Activities

  • これまでに「機能有機化学」、「先端有機化学」、「有機機器分析」、「有機構造物性論」、「有機元素化学」、「有機金属化学」など、大学院生を対象とした授業を受け持ってきており、2024年度は、「機能有機化学」や「有機機器分析」、「有機金属化学」を担当する。講義のみならず演習も交えることにより、学生さんにしっかりと知識を身に着けてもらうとともに、その原理や意義に関する理解を深めてもらうべく授業を行なっている。また、研究室での研究を通じたより実践的な教育も重要だと考えており、日常やセミナーなどでのディスカッションを中心に、教育指導にも力を入れている。

Class subject

  • 有機金属化学

    2024.10 - 2025.3   Second semester

  • 有機機器分析

    2024.4 - 2024.6   Spring quarter

  • 機能有機化学

    2024.4 - 2024.6   Spring quarter

  • 有機金属化学

    2023.10 - 2024.3   Second semester

  • 総合理工学修士実験

    2023.4 - 2024.3   Full year

  • 総合理工学修士実験

    2023.4 - 2024.3   Full year

  • 総合理工学修士演習

    2023.4 - 2024.3   Full year

  • 物質理工学修士実験

    2023.4 - 2024.3   Full year

  • 物質理工学修士演習

    2023.4 - 2024.3   Full year

  • 物質理工学第一特別講究

    2023.4 - 2024.3   Full year

  • 総合理工学修士演習

    2023.4 - 2024.3   Full year

  • 総合理工学修士実験

    2023.4 - 2024.3   Full year

  • 総合理工学修士演習

    2023.4 - 2024.3   Full year

  • 機能有機化学

    2023.4 - 2023.6   Spring quarter

  • 有機機器分析 ei

    2023.4 - 2023.6   Spring quarter

  • 有機金属化学

    2022.10 - 2023.3   Second semester

  • 総合理工学修士実験

    2022.4 - 2023.3   Full year

  • 総合理工学修士演習

    2022.4 - 2023.3   Full year

  • 機能有機化学

    2022.4 - 2022.6   Spring quarter

  • 有機機器分析 ei

    2022.4 - 2022.6   Spring quarter

  • 有機金属化学

    2021.10 - 2022.3   Second semester

  • 物質理工学修士演習第一

    2021.4 - 2022.3   Full year

  • 物質理工学第一特別講究

    2021.4 - 2022.3   Full year

  • 物質理工学第一特別講究

    2021.4 - 2022.3   Full year

  • 物質理工学修士実験第一

    2021.4 - 2022.3   Full year

  • 機能有機化学

    2021.4 - 2021.6   Spring quarter

  • 有機機器分析 ei

    2021.4 - 2021.6   Spring quarter

  • 機能有機化学

    2020.10 - 2021.3   Second semester

  • 機能有機化学

    2020.10 - 2021.3   Second semester

  • 有機元素化学

    2020.6 - 2020.8   Summer quarter

  • 有機元素化学

    2020.6 - 2020.8   Summer quarter

  • 生体有機化学

    2020.4 - 2021.3   Full year

  • 生体有機化学

    2020.4 - 2021.3   Full year

  • 物質理工学修士実験第一

    2020.4 - 2021.3   Full year

  • 物質理工学修士演習第一

    2020.4 - 2021.3   Full year

  • Experiments on Molecular and Material Sciences

    2020.4 - 2021.3   Full year

  • Exercises on Molecular and Material Sciences

    2020.4 - 2021.3   Full year

  • 物質理工学修士実験第一

    2020.4 - 2021.3   Full year

  • 物質理工学修士演習第一

    2020.4 - 2021.3   Full year

  • 有機構造物性論

    2020.4 - 2020.6   Spring quarter

  • 有機構造物性論

    2020.4 - 2020.6   Spring quarter

  • 機能有機化学

    2019.10 - 2020.3   Second semester

  • 立体制御合成論

    2019.4 - 2020.3   Full year

  • 物質理工学修士実験第一

    2019.4 - 2020.3   Full year

  • 物質理工学修士演習第一

    2019.4 - 2020.3   Full year

  • 機能有機化学

    2018.10 - 2019.3   Second semester

  • 立体制御合成論

    2018.4 - 2019.3   Full year

  • 物質理工学修士演習第一

    2018.4 - 2019.3   Full year

  • 物質理工学修士実験第一

    2018.4 - 2019.3   Full year

  • 異分野特別演習

    2017.10 - 2018.3   Second semester

  • 機能有機化学

    2017.10 - 2018.3   Second semester

  • 立体制御合成論

    2017.4 - 2018.3   Full year

  • 物質理工学修士演習第一

    2017.4 - 2018.3   Full year

  • 物質理工学修士実験第一

    2017.4 - 2018.3   Full year

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FD Participation

  • 2024.10   Role:Moderator   Title:先導研FD

    Organizer:[Undergraduate school/graduate school/graduate faculty]

  • 2023.3   Role:Participation   Title:先導研FD

    Organizer:[Undergraduate school/graduate school/graduate faculty]

  • 2022.1   Role:Participation   Title:先導研FD

    Organizer:[Undergraduate school/graduate school/graduate faculty]

  • 2021.1   Role:Participation   Title:先導研FD

    Organizer:[Undergraduate school/graduate school/graduate faculty]

  • 2020.1   Role:Participation   Title:第2回先導研FD

    Organizer:[Undergraduate school/graduate school/graduate faculty]

  • 2019.5   Role:Participation   Title:第1回先導研FD

    Organizer:[Undergraduate school/graduate school/graduate faculty]

  • 2019.1   Role:Participation   Title:第2回先導研FD

    Organizer:[Undergraduate school/graduate school/graduate faculty]

  • 2018.7   Role:Participation   Title:第1回先導研FD

    Organizer:[Undergraduate school/graduate school/graduate faculty]

  • 2018.1   Role:Participation   Title:第2回先導研FD

    Organizer:[Undergraduate school/graduate school/graduate faculty]

  • 2017.5   Role:Participation   Title:第1回先導研FD

    Organizer:[Undergraduate school/graduate school/graduate faculty]

  • 2017.4   Role:Participation   Title:新任教員研修

    Organizer:University-wide

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Visiting, concurrent, or part-time lecturers at other universities, institutions, etc.

  • 2022  京都大学大学院工学研究科  Classification:Part-time lecturer  Domestic/International Classification:Japan 

    Semester, Day Time or Duration:2022年10月14日(金)

  • 2021  福岡大学大学院理学研究科  Classification:Part-time lecturer  Domestic/International Classification:Japan 

    Semester, Day Time or Duration:2021年9月14日(火)-15日(水)

  • 2020  名古屋大学大学院工学研究科  Classification:Part-time lecturer  Domestic/International Classification:Japan 

    Semester, Day Time or Duration:2020年10月9日

  • 2019  東京大学大学院理学系研究科  Classification:Part-time lecturer  Domestic/International Classification:Japan 

    Semester, Day Time or Duration:2019年12月5-6日