DOI： 10.1093/chemle/upae053

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DOI： 10.1093/chemle/upae053

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Authorship：Last author   Language：Japanese   Publishing type：Research paper (other academic)  

Authorship：Lead author   Language：Japanese   Publishing type：Research paper (scientific journal)  

Other Link： https://www.jstage.jst.go.jp/browse/kakyoshi/-char/ja

Language：Japanese   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

Herein, we report a heterogeneous cobalt-catalyzed H2Sreagent-free synthetic method for 1,2-bis(2,4,4-trimethylpentan-2-yl)-
polysulfanes, which have been used as extreme-pressure additives in the field of tribology and have been produced worldwide in the tens ofthousands of tonnes per year. The current industrial synthetic processes typically use hydrogen sulfide as the reductant, but improvements are needed in terms of the toxicity and the cost associated with safety control.
The present reaction with Co3O4 and Na-X zeolite as catalysts provides the corresponding polysulfanes with three to eight sulfur atoms from diisobutylene, hydrogen, and elemental sulfur in up to 88% yield under neat reaction conditions. Experimental and density functional theory (DFT) mechanistic investigations provide insights into the roles of Na-X
zeolite and cobalt catalysts. The DFT calculations suggest that heterolytic H2 activation with cobalt polysulfide species and
subsequent protonation of alkenes and the C−S bond formation take place in a single step by a terminal SSH group in the cobalt polysulfide species, which provides a reasonable interpretation of the observed Markovnikov selectivity.

DOI： 10.1021/acscatal.3c03545

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Gold nanoparticles supported on SiO2, Al2O3, TiO2, and carbon (Maxsorb, Ketjen black and Shirasagi New Gold) were prepared by impregnation and solid grinding methods using N-heterocyclic carbene (NHC)-Au complexes as precursors. A total of nine NHC-Au complex precursors were tested by impregnation and solid grinding method, and [Au(OH)(IPr)] (IPr = 1,3-bis(2,6-diisopropylphenyl)1,3-dihydro-2H-imidazol-2-ylidene) complex led to (1–2 nm) particle sizes by both methods. The prepared catalysts were characterized by XRD (X-ray diffraction), HAADF-STEM (high-angle annular dark-field scanning transmission electron microscopy), in situ XAFS (X-ray absorption fine structure), etc. In addition, [Au(OH)(IPr)] and its impregnated [Au(OH)(IPr)]/SiO2 were subjected to TG-DTA (thermogravimetry analysis-differential thermal analysis) and in situ XAFS analysis under calcination conditions, respectively. Moreover, the obtained supported Au nanoparticles (NPs) were effective as catalysts for low-temperature CO oxidation, intramolecular cyclization of alkynyl carboxylic acids, and isomerization of allylic esters. Their results suggested that the reduction of [Au(OH)(IPr)] proceeds rapidly from around 300°C, and the residual ligands should be attached to the surface of the Au NPs and protect them from drastic agglutination. These results reveal that properly designed NHC-Au complexes can facilitate the preparation of supported Au NP catalysts with small particle sizes and high activities.

DOI： 10.1016/j.mcat.2023.113460

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Language：Japanese   Publishing type：Research paper (scientific journal)   Publisher：Royal Society of Chemistry (RSC)  

[Zn(dmpz)₂NDI]_n-MOF serves as a high rate capable anode for aqueous batteries thanks to its large pores. K⁺-based aqueous electrolytes may exploit its maximum rate performance, possibly because its hydrated ions can move freely in the electrode.

DOI： 10.1039/d3ra03187j

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Language：Japanese   Publisher：The Society of Synthetic Organic Chemistry, Japan  

<p>An ester group is one of ubiquitous and important functional groups in the field of organic chemistry. Stereoselective transformations of substrates having ester groups using artificial catalysts such as metal complexes and organocatalysts have been developed such as 1,4-addition of α,β-unsaturated esters and functionalizations at α-carbon of esters. However, stereoselective transformations of the ester group itself have been still highly limited.</p><p>Hydrolase-catalyzed asymmetric hydrolysis of esters, which is a basic and important reaction categorized as the latter reaction type, has long been studied, and widely used from the lab scale to the industrial scale synthesis. However, enzymatic reactions generally have several issues such as their low specific activity and high cost. Under these circumstances, we hypothesized that stereoselective base hydrolysis of esters would be achieved by using liquid-liquid biphasic system with chiral onium salt catalysts. Herein, we describe the asymmetric base hydrolysis of esters using chiral onium salt catalysts derived from Cinchona alkaloids and chiral amino acids as well as the related dynamic kinetic resolution of azlactones via phase-transfer catalytic base alcoholysis. In addition, we also demonstrated the computational investigations using ConFinder program with pseudo-transition state conformational search (PTSCS) method.</p>

DOI： 10.5059/yukigoseikyokaishi.81.798

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CiNii Research

Language：Others   Publishing type：Research paper (scientific journal)   Publisher：Wiley  

Abstract

Heterogeneous noble metal catalysts exhibit various functions. Although their redox functions have been extensively studied, we focused on their soft Lewis acid functions. Supported Au, Pt, and Pd catalysts electrophilically attack the π‐electrons of soft bases such as alkynes, alkenes, and aromatic compounds to perform addition and substitution reactions. Hydroamination, intramolecular cyclization of alkynyl carboxylic acids, isomerization of allylic esters, vinyl exchange reactions, Wacker oxidation, and oxidative homocoupling of aromatics are introduced based on a discussion of the active species and reaction mechanisms. Furthermore, the adsorption of sulfur compounds, which are soft bases, onto the supported AuNPs is discussed. The adsorption and removal of 1,3‐dimethyltrisulfane (DMTS), which is the compound responsible for the stale odor of “hine‐ka” in alcoholic beverages, particularly Japanese sake, is described.

DOI： 10.1002/tcr.202300148

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To extend the lifetime and improve the safety of lithium-ion batteries, the decomposition mechanism of electrolytes in lithium-ion batteries was kinetically and stereospecifically studied in simplified reaction systems, which were in contact with the charged positive electrodes including Li1-x CoO2 as an active material removed from batteries. By identifying the products, mainly vinylene carbonate (VC) was detected by gas chromatography as an oxidation product of ethylene carbonate (EC). The kinetic isotope effects of the reaction were evaluated using EC and deuterium-labeled ECD4. The kH/kD was found to be 2.9 suggesting the C-H bond cleavage step was irreversible and corresponds to the rate-determining step of the overall process in the reaction. Also, Arrhenius and Eyring plots and stereospecific studies using syn-substituted EC-D2 indicated that the transition state has a rigid structure and that the elimination of hydrogens from EC proceeded mainly via syn stereochemistry. Upon a change in the charge potential of Li1-xCoO2 from 4.5V to 4.1V, the rate of formation of VC decreased.

DOI： 10.1246/bcsj.20230027

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Journal of Organic Chemistry  

A detailed theoretical mechanistic investigation on the dynamic kinetic resolution of N-protected amino acid esters using phase-transfer catalysts is described. Semiautomatic exhaustive conformation search of transition state (TS)-like structures were carried out using the ConFinder program and the pseudo-TS conformational search (PTSCS) method. This conformational search method successfully provided reasonable TS structures for determining the stereoselectivity in the asymmetric base hydrolysis of hexafluoroisopropyl (HFIP) esters as well as the racemization mechanism. Furthermore, the independent gradient model (IGM) analysis of the TS structures suggested that the H-bonding interactions with the oxyanion hole and π-stacking interactions are the common important features of the proposed TS structures that determine the stereoselectivity.

DOI： 10.1021/acs.joc.2c02352

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The effect of the Pt shell thickness on the oxygen reduction reaction (ORR) of a Pd@Pt core-shell catalyst was studied using surface science technics and computational approaches. We found Pt shells on Pd rods to be negatively charged because of charge transfer from the Pd substrate when the shell thicknesses were 0.5 or 1 monolayer (ML). The activities of the ORR of the model surface with a Pt shell of 0.5 or 1 ML were similar and more than twice the activities of a Pt/C or Pt rod. The relationship between the ORR activity and the thickness of the Pt shell was the exact opposite of the relationship between the Pt binding energy and the Pt shell thickness. The indication was that more negatively charged Pt had higher ORR activity. Density functional theory calculations confirmed that a single layer of Pt atoms located on Pd was negatively charged compared to pure Pt and resulted in a lower barrier to the rate-limiting step of the ORR.

DOI： 10.1002/cphc.202200389

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Language：English   Publisher：Royal Society of Chemistry (RSC)  

A metal–organic framework (MOF) having a redox active 1,4,5,8-naphthalenetetracarboxdiimide (NDI) derivative in its organic linker shows excellent rate performance as an electrode material for aqueous batteries thanks to its large pores. Among aqueous electrolytes examined, K+-based ones exhibit the highest rate performance, which is caused by the highest mobility of the smallest hydrated K+ ion not only in the aqueous electrolyte but also in the electrode. Since the use of a counter electrode with insufficiently small pores for the full-cell configuration offsets this merit, our study may lead to a conclusion that the maximum rate performance for aqueous batteries will be accomplished only through further elaboration of both electrode materials with sufficiently large pores, in which hydrated ions can travel equally fast as those in the electrolyte.

CiNii Research

Language：Others   Publishing type：Research paper (scientific journal)   Publisher：Elsevier BV  

When producing liquid fuels from petroleum, hydrodesulfurization methods reduce the concentration of sulfur to ≤10 mg(S)/L (weight/volume concentration of sulfur), namely, ≤ 0.31 mmol/L. Dibenzothiophene derivatives (DBTs), which are known as particularly difficult desulfurizing substances, have been decomposed reductively in severe conditions of high temperatures (270–372 °C) and high pressure (50–102 atm of H2). In this study, we developed a UV light irradiation-based desulfurization method for aromatic sulfur compounds such as benzothiophene derivatives (BTs) and DBTs under room temperature and atmospheric pressure without the use of catalysts or additives. This method is simple, location-independent, and low-cost, and has low environmental impact. BTs and DBTs completely decomposed in approximately 8 h and 16 h, respectively, under ultraviolet (UV) light irradiation (λ = 254 nm) from a 8 W lamp. The yellow precipitates that were produced upon decomposition were confirmed to be sulfur allotropes (Sn). The residual hydrocarbon portion of DBT after sulfur removal was determined to be benzene. The decomposition reaction was determined to exhibit pseudo-first-order reaction. DFT calculations confirmed the degradation mechanism as follows: UV light irradiation induces a photochemically excited triplet state of DBTs. The excited DBTs reacts with O2 to form a π-complex, which isomerizes to a more stable σ-complex. The DBTs-O2 (σ-complex) then reacts with free DBTs to afford two molecules of dibenzothiophene-5-oxide derivatives (DBTOs), which are excited to singlet states on photoirradiation. The excited DBTOs isomerize through a minimum energy intersection eventually to dibenzofuran episulfides from which sulfur extrusion occurs.

DOI： 10.1016/j.jclepro.2022.133402

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β-Hydroxy β-methylbutyric acid (HMB) is expected as a promising therapeutic agent or a supplement. For industrial production of HMB, Pt-catalyzed aerobic oxidation of isoprene glycol is a potent synthetic method. However, the previous report using Pt-Bi catalyst supported on active carbon suffered from low tolerance to high substrate concentration conditions, which leads to low volumetric productivity. Herein, we report aerobic oxidation of isoprene glycol using Pt-Bi catalysts supported on ZrO2 or TiO2, showing high tolerance to the high substrate concentration conditions. In addition, these catalysts exhibited high recyclability. Scanning transmission electron microscopy analyses suggested the Pt-Bi species supported on ZrO2 or TiO2 are less likely to aggregate than those supported on activated carbon. Additionally, these metal oxides supported catalysts showed lower metal leaching than the carbon supported catalysts. Besides, the results of the various control experiments indicated the prevention of dehydration of an aldehyde intermediate is important for further improvement.

DOI： 10.1016/j.apcata.2022.118781

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Zirconia-supported sodium-salt-modified Au(0) nanoparticles (NPs) (Na-Au/ZrO2) catalyst was prepared, and it was stable and recyclable in the intramolecular cyclization of alkynoic acids. In particular, the effect of sodium species in Na-Au/ZrO2, which has been overlooked in previous studies, was studied, and they were found to play an essential role in the reaction. In addition, the relationship between the kinetics and size of Au NPs revealed that the active sites of the catalyst are located on the surface of the supported Au NPs. Moreover, detailed kinetic studies revealed that the cyclization was a zero-order reaction with respect to substrate concentration, and the rate-determining step of the reaction is presumed to be protodeauration. The maximum turnover number (TON) of the reaction of 5-hexynoic acid in a continuous flow reactor exceeded 9000, which is the highest TON obtained in the presence of a heterogeneous Au catalyst.

DOI： 10.1016/j.apcata.2022.118765

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Metal oxides supported platinum catalysts with residual chloride are known to be reusable soft Lewis acid catalysts for the isomerization of allylic esters. To deepen the understanding of the industrial application of the catalytic system and optimize the catalyst design, an investigation on the reusability and deactivation mechanism of supported platinum catalysts in the isomerization of but-3-ene-1,2-diyl diacetate was conducted. A great reactivation effect was observed by treating the used catalysts with HCl, rather than that of calcination. Pt-Cl/CeO2 showed the best reusability among the catalysts prepared with other metal oxides, and it was uncovered that the reduction of PtOxCly species should be the main reason for deactivation with the assistance of X-ray absorption fine structure (XAFS) analysis. Besides, a relatively stable state was also observed from the XAFS spectra of Pt-Cl/CeO2 catalysts in the reusing test, and it could effectively prevent the active species from further deactivation. Furthermore, in an extended evaluation of the stability of the catalysts, reusability, and a limited deactivation were also verified through a 10-run batch reaction. Additionally, the continuous flow reaction was also proven to be feasible.

DOI： 10.1016/j.cattod.2022.06.007

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Language：Others   Publishing type：Research paper (scientific journal)   Publisher：Chemistry - An Asian Journal  

Carbon-nitrogen bond formation is an important method on both laboratory and industrial scales because it realizes the production of valuable pharmaceuticals, agrochemicals, and fine chemicals. Direct reductive N-alkylation of amines with carbonyl compounds via intermediary imine compounds, especially under catalytic hydrogenation conditions, is one of the most convenient, economical, and environmentally friendly methods for this process. Here we report a novel palladium species on zirconia having specific activity towards hydrogenation of imines but other carbonyl groups remaining intact. The present catalytic property offers a practical synthetic method of functionalized secondary amines by reductive N-alkylation under mild conditions with high atom-efficiency. Mechanistic studies revealed that the catalytically active species is the palladium cluster, which is generated in situ from molecular palladium complexes on the support by exposure to atmospheric hydrogen. These fundamental findings are expected to progress in developing novel cluster catalysts for chemical processes directed towards a sustainable society.

DOI： 10.1002/asia.202101243

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Convenient catalytic synthetic methods for the preparation of unsymmetrical disulfanes are described. Na-exchanged X type zeolite (Na-X), commercially available as MS-13X, effectively catalyzes thiol-disulfane exchange reactions with 1.0 equivalent of thiols and 2.5–3.0 equivalents of disulfanes at 10 °C to room temperature under air. The reactions of sterically-hindered disulfanes or electron-deficient thiol substrates require high temperatures under inert atmospheres to maintain the good product yields. Various functionalized thiols and disulfanes are tolerant in the present catalytic systems, affording the corresponding unsymmetrical disulfanes in good-to-high yields (up to 96 %). The Na-X catalyst was successfully recycled 10 times without loss of yield. Preliminary mechanistic studies suggest the involvement of base-catalyzed SN2-S displacement and/or addition-elimination mechanisms, assisted by hydrogen-bonding interactions.

DOI： 10.1002/cctc.202101092

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Heterogeneous acid and base catalysts play a crucial role in many important chemical processes. Hard Lewis and Brønsted acid catalysts like silica-alumina and zeolites have been widely applied in numerous reactions; however, developing reusable and active soft Lewis acid catalysts remain a challenge. Herein, we demonstrate for the first time that a highly dispersed supported platinum catalyst can act as a heterogeneous soft Lewis acid. High turnover numbers and reusability were observed in the isomerization of allylic esters under solvent-free conditions. Moreover, the as-prepared catalysts are characterized by X-ray photoelectron spectroscopy (XPS) and X-ray absorption fine structure (XAFS), revealing that the highly dispersed Pt clusters with Pt–Cl bonds play a key role in the high activity. The residual chloride anion enhances the Lewis acidity of the Pt metal center and thus improves the catalytic activity. Simultaneously, the high catalytic activity of Pt/CeO2 with residual chloride and the soft Lewis acid mechanism are also proved by density functional theory (DFT) calculations based on the model reaction.

DOI： 10.1016/j.apcatb.2021.120333

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Phase-transfer catalytic asymmetric alcoholysis of azlactones via dynamic kinetic resolution proceeded for a wide range of alcohols and azlactones, affording the corresponding α-chiral amino acid esters in up to 98% yield and up to 99:1 er. In addition, this catalytic system was also applied to the asymmetric alcoholysis of N-benzoyl amino acid hexafluoroisopropyl ester providing the desired product in good yield with high stereoselectivity (71% yield, 98:2 er). The catalyst loading could be reduced to 0.1 mol % without significant loss of stereoselectivity (turnover number = 411). Furthermore, a gram-scale reaction and transformations of the enantioenriched products involving hydrogenolysis, LAH-reduction, and Suzuki-Miyaura coupling reactions were successfully achieved. Detailed computational studies using a pseudotransition state (pseudo-TS) conformational search with ConFinder and density functional theory (DFT) calculations indicated a TS model that accounted for the origin of the stereoselectivity. In this TS model, water or alcohol molecules activate the azlactone substrate by H-bonding with the nitrogen atom, and concomitant accumulated weak interactions, including H-bonding interactions, C-H-π, and π-πinteractions, stabilize the TS, leading to the major enantiomer.

DOI： 10.1021/acscatal.1c03076

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The process of C-H functionalization has been extensively studied as a direct C-C bond-forming reaction with high atomic efficiency. Efforts have also been made on such reactions by using supported catalysts, which are superior in terms of catalyst separation from the reaction mixture and reusability. In this review, an overview of C-H functionalization reactions, especially those involving Pd- and Au-supported catalysts, is presented. In particular, we discuss reaction mechanisms, active species, leaching, reusability, etc. 1 Introduction 2 Types of Supported Metal Catalysts and Their Active Species 3 Modes of C-H Bond Activation 4 Oxidative C-H C-H Coupling of Aryl Compounds 5 C-H C-H Coupling Where One Side Is Aromatic 6 C-H Acylation of Aromatic Compounds and Related Reactions 7 Conclusion.

DOI： 10.1055/a-1468-1455

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A flow manufacturing process was investigated for the synthesis of Pd@Pt core-shell nanoparticles (NPs) with high productivity and exact structural control. Pd@Pt core-shell NPs were successfully synthesized in a flow reactor using polyvinylpyrrolidone (PVP) as a capping agent. However, the oxygen reduction reaction (ORR) activity of the Pd@Pt/PVP/C catalyst was found to be significantly lower than that of commercial Pt/C as the remaining PVP inhibited ORR. In order to improve ORR activity, it is necessary to support the highly dispersed Pd@Pt NPs on activated carbon without the use of PVP. Cyclic voltammetry, transmission electron microscopy, and X-ray absorption fine structure analyses showed that Pd@Pt NPs could be uniformly dispersed on activated carbon by adding bis(2-methoxyethyl) ether (diglyme) as a capping agent. The particle size and core-shell structure of the Pd@Pt NPs did not differ significantly between the NPs synthesized with PVP or diglyme, indicating that advanced structural control was possible without PVP. Furthermore, the mass activity per Pt weight of the Pd@Pt/C catalyst using diglyme was found to be 1.8-fold higher than that of Pt/C. We thus succeeded in synthesizing Pd@Pt core-shell NPs with precisely controlled structure and high ORR activity by flow process.

DOI： 10.1016/j.colsurfa.2021.126607

Language：Japanese   Publishing type：Research paper (scientific journal)  

DOI： doi.org/10.1016/j.colsurfa.2021.126607

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© 2020 Elsevier Ltd Ruthenium oxide catalysts supported on various metal oxides, such as zirconia, ceria, and alumina, were prepared by an impregnation method using RuCl3·3H2O as a precursor. Local structures of the supported Ru oxide and oxidation states of Ru species were analyzed by in situ Ru K-edge X-ray absorption fine structure measurements. Small RuO2 particles were highly dispersed on zirconia and ceria. On the other hand, bulk RuO2 was deposited on alumina. Enantioselective hydrogenation of diethyl itaconate was achieved by combining the supported RuO2 catalysts with chiral ligands. The 1 wt% RuO2 supported on zirconia provided 95% ee and 99% yield. The Ru oxide was partially reduced during the reaction.

DOI： 10.1016/j.radphyschem.2019.02.017

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Au-Ni bimetallic nanoparticles catalyze the hydrogenolysis of the hydroxy group of benzylic alcohols by activating H2 with dichloroethane solvent. To propose a working hypothesis for their reaction mechanism, we performed theoretical calculations for the hydroxylation of methyl vinyl carbinol over the Au1Ni19 cluster. The results showed that there're two reaction cycles, depending on the presence of HCl. Firstly, the solvent acted as a sacrificial reagent to produce the carbocation intermediate, while HCl was produced in other reaction. It was found that the presence of the exposed Au site played an important role for producing HCl and subsequent hydrogenolysis.

DOI： 10.1016/j.cplett.2020.137773

Language：Japanese   Publishing type：Research paper (scientific journal)  

Language：Japanese   Publishing type：Research paper (scientific journal)  

DOI： 10.1246/cl.190868

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DOI： doi.org/10.1016/j.cplett.2020.137773

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DOI： DOI: 10.1055/a-1468-1455

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Study for practical application of supported gold nanoparticles for removal of DMTS responsible for hineka in sake

Language：English   Publishing type：Research paper (scientific journal)  

Surface Modification of a Supported Pt Catalyst Using Ionic Liquids for Selective Hydrodeoxygenation of Phenols into Arenes under Mild Conditions
The selective and efficient removal of oxygenated groups from lignin-derived phenols is a critical challenge to utilize lignin as a source for renewable aromatic chemicals. This report describes how surface modification of a zeolite-supported Pt catalyst using ionic liquids (ILs) remarkably increases selectivity for the hydrodeoxygenation (HDO) of phenols into arenes under mild reaction conditions using atmospheric pressure H2. Unmodified Pt/H-ZSM-5 converts phenols into aliphatic species as the major products along with a slight amount of arenes (10 &#37; selectivity). In contrast, the catalyst modified with an IL, 1-butyl-3-methylimidazolium triflate, keeps up to 76 &#37; selectivity for arenes even at a nearly complete conversion of phenols. The IL on the surface of Pt catalyst may offer the adsorption of phenols in an edge-to-face manner onto the surface, thus accelerating the HDO without the ring hydrogenation.

DOI： 10.1002/chem.201902668

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The selective and efficient removal of oxygenated groups from lignin-derived phenols is a critical challenge to utilize lignin as a source for renewable aromatic chemicals. This report describes how surface modification of a zeolite-supported Pt catalyst using ionic liquids (ILs) remarkably increases selectivity for the hydrodeoxygenation (HDO) of phenols into arenes under mild reaction conditions using atmospheric pressure H₂. Unmodified Pt/H-ZSM-5 converts phenols into aliphatic species as the major products along with a slight amount of arenes (10 % selectivity). In contrast, the catalyst modified with an IL, 1-butyl-3-methylimidazolium triflate, keeps up to 76 % selectivity for arenes even at a nearly complete conversion of phenols. The IL on the surface of Pt catalyst may offer the adsorption of phenols in an edge-to-face manner onto the surface, thus accelerating the HDO without the ring hydrogenation.

DOI： 10.1002/chem.201902668

Language：English   Publishing type：Research paper (scientific journal)  

The selective and efficient removal of oxygenated groups from lignin-derived phenols is a critical challenge to utilize lignin as a source for renewable aromatic chemicals. This report describes how surface modification of a zeolite-supported Pt catalyst using ionic liquids (ILs) remarkably increases selectivity for the hydrodeoxygenation (HDO) of phenols into arenes under mild reaction conditions using atmospheric pressure H₂. Unmodified Pt/H-ZSM-5 converts phenols into aliphatic species as the major products along with a slight amount of arenes (10 % selectivity). In contrast, the catalyst modified with an IL, 1-butyl-3-methylimidazolium triflate, keeps up to 76 % selectivity for arenes even at a nearly complete conversion of phenols. The IL on the surface of Pt catalyst may offer the adsorption of phenols in an edge-to-face manner onto the surface, thus accelerating the HDO without the ring hydrogenation.

DOI： 10.1002/chem.201902668

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© 2019 Elsevier B.V. The additive effect of amines on the supported PdO catalyzed-dihydroxylation of buta-1,3-diene is first examined. The significant enhancement of the synthetic efficiency for the diol products is achieved by the addition of less hindered strong bases, such as morpholines and N-methylimidazole. Notably, we found that the amine additive is indispensable to keep the catalytic activity during the recycling test, which is never mentioned in previous reports. Furthermore, both the fresh and spent catalysts are characterized by attenuated total reflection infrared (ATR-IR) observation and X-ray absorption fine structure (XAFS) measurements.

DOI： 10.1016/j.mcat.2019.110502

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The additive effect of amines on the supported PdO catalyzed-dihydroxylation of buta-1,3-diene is first examined. The significant enhancement of the synthetic efficiency for the diol products is achieved by the addition of less hindered strong bases, such as morpholines and N-methylimidazole. Notably, we found that the amine additive is indispensable to keep the catalytic activity during the recycling test, which is never mentioned in previous reports. Furthermore, both the fresh and spent catalysts are characterized by attenuated total reflection infrared (ATR-IR) observation and X-ray absorption fine structure (XAFS) measurements.

DOI： 10.1016/j.mcat.2019.110502

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The additive effect of amines on the supported PdO catalyzed-dihydroxylation of buta-1,3-diene is first examined. The significant enhancement of the synthetic efficiency for the diol products is achieved by the addition of less hindered strong bases, such as morpholines and N-methylimidazole. Notably, we found that the amine additive is indispensable to keep the catalytic activity during the recycling test, which is never mentioned in previous reports. Furthermore, both the fresh and spent catalysts are characterized by attenuated total reflection infrared (ATR-IR) observation and X-ray absorption fine structure (XAFS) measurements.

DOI： 10.1016/j.mcat.2019.110502

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Bifunctional phosphonium/thioureas derived from tert-leucine behaved as highly selective catalysts for enantioselective protonation of enol esters, providing α-chiral ketones in yields of up to 99% with high enantioselectivities (up to 98.5:1.5 er). Control experiments clarified that a bulky tert-butyl group and phosphonium and thiourea moieties were necessary to achieve such high stereoselectivity. In addition, mechanistic investigations indicated the catalyst was converted to the corresponding betaine species, which served as a monomolecular catalyst.

DOI： 10.1021/acs.orglett.9b01216

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Palladium (Pd) clusters on zirconia (ZrO₂) and single Pd atoms on ceria (CeO₂) exhibited high catalytic activity and selectivity for decarbonylation of furfural to furan without additives in the liquid phase. To study the active size of Pd and changes in chemical states or structures during the reaction, in-situ X-ray absorption fine structure (XAFS) measurements were conducted. The size of Pd clusters consisting of less than 10 Pd atoms was maintained on ZrO₂ during the reaction. In contrast, single Pd atoms were aggregated during heating and only Pd clusters consisting of 13 atoms were present after the reaction. According to the in-situ XAFS results, the size of Pd particles did not gradually increase to Pd₁₃ clusters. Instead, Pd₁₃ clusters were partly formed from the beginning of the reaction, and the proportion of Pd₁₃ clusters increased with time while keeping the size of Pd₁₃ clusters. This result suggests that a single Pd atom is inactive, but Pd clusters are active for decarbonylation. Ab-initio calculation revealed that ZrO₂ (1 1 1) surface had lower adsorption and migration energies than CeO₂ (1 1 1), implying that Pd was easily diffused on the surface and stabilized as small Pd clusters.

DOI： 10.1016/j.jcat.2019.04.041

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Bifunctional phosphonium/thioureas derived from tert-leucine behaved as highly selective catalysts for enantioselective protonation of enol esters, providing α-chiral ketones in yields of up to 99% with high enantioselectivities (up to 98.5:1.5 er). Control experiments clarified that a bulky tert-butyl group and phosphonium and thiourea moieties were necessary to achieve such high stereoselectivity. In addition, mechanistic investigations indicated the catalyst was converted to the corresponding betaine species, which served as a monomolecular catalyst.

DOI： 10.1021/acs.orglett.9b01216

Language：English   Publishing type：Research paper (scientific journal)  

The anti-Markovnikov addition of H₂O to alkenes to directly bring in primary alcohols has been considered one of the “10 challenges in catalysis” in the 1990s, but the challenging issue has still remained unsolved over the past few decades, particularly in terms of developing an atom-efficient synthetic strategy. In this context, we introduce a novel access for the transformation of terminal alkenes with H₂O into the corresponding primary alcohols over metal oxide-supported Pd catalysts, employing O₂ as the sole oxidant. Direct and efficient synthesis of cinnamyl alcohol from allylbenzene and H₂O was initially achieved as a fine chemical example over Pd(NO₃)₂/CeO₂-ZrO₂, and the target saturated alcohol (3-phenylpropan-1-ol) was obtained as the anti-Markovnikov selective product from a “one-pot” process using H₂ as the reductant. The Pd(NO₃)₂/CeO₂-ZrO₂ was characterized by HAADF-STEM, XRD and X-ray absorption fine structure (XAFS) analyses, indicating that the molecular Pd(NO₃)₂ is probably deposited as it is on the support, which likely plays an important role to promote this reaction. In the second part, Pd(NO₃)₂/CeO₂-ZrO₂ and other supported Pd catalysts were applied for the transformation of 1,3-butadiene into 2-butene-1,4-diol in a batch reactor. Besides, butane-1,4-diol, which is an important industrial material, was efficiently produced by the simple hydrogenation of 2-butene-1,4-diol in a “one-pot” manner. Significantly, the development of the reaction catalyzed by supported Pd in a gas flow reactor bestows great potential to further industrial applications. Additionally, the adsorption structure of 1,3-butadiene on Pd(111) was confirmed as the s-trans form by infrared reflection absorption spectroscopy (IRAS) measurements. The change in the electronic states of surface Pd atoms upon oxygen adsorption was observed by X-ray photoelectron spectroscopy (XPS).

DOI： 10.1016/j.apcatb.2019.01.031

Language：English   Publishing type：Research paper (scientific journal)  

Palladium (Pd) clusters on zirconia (ZrO₂) and single Pd atoms on ceria (CeO₂) exhibited high catalytic activity and selectivity for decarbonylation of furfural to furan without additives in the liquid phase. To study the active size of Pd and changes in chemical states or structures during the reaction, in-situ X-ray absorption fine structure (XAFS) measurements were conducted. The size of Pd clusters consisting of less than 10 Pd atoms was maintained on ZrO₂ during the reaction. In contrast, single Pd atoms were aggregated during heating and only Pd clusters consisting of 13 atoms were present after the reaction. According to the in-situ XAFS results, the size of Pd particles did not gradually increase to Pd₁₃ clusters. Instead, Pd₁₃ clusters were partly formed from the beginning of the reaction, and the proportion of Pd₁₃ clusters increased with time while keeping the size of Pd₁₃ clusters. This result suggests that a single Pd atom is inactive, but Pd clusters are active for decarbonylation. Ab-initio calculation revealed that ZrO₂ (1 1 1) surface had lower adsorption and migration energies than CeO₂ (1 1 1), implying that Pd was easily diffused on the surface and stabilized as small Pd clusters.

DOI： 10.1016/j.jcat.2019.04.041

Language：English   Publishing type：Research paper (scientific journal)  

Bifunctional phosphonium/thioureas derived from tert-leucine behaved as highly selective catalysts for enantioselective protonation of enol esters, providing α-chiral ketones in yields of up to 99% with high enantioselectivities (up to 98.5:1.5 er). Control experiments clarified that a bulky tert-butyl group and phosphonium and thiourea moieties were necessary to achieve such high stereoselectivity. In addition, mechanistic investigations indicated the catalyst was converted to the corresponding betaine species, which served as a monomolecular catalyst.

DOI： 10.1021/acs.orglett.9b01216

Language：English   Publishing type：Research paper (scientific journal)  

The anti-Markovnikov addition of H₂O to alkenes to directly bring in primary alcohols has been considered one of the “10 challenges in catalysis” in the 1990s, but the challenging issue has still remained unsolved over the past few decades, particularly in terms of developing an atom-efficient synthetic strategy. In this context, we introduce a novel access for the transformation of terminal alkenes with H₂O into the corresponding primary alcohols over metal oxide-supported Pd catalysts, employing O₂ as the sole oxidant. Direct and efficient synthesis of cinnamyl alcohol from allylbenzene and H₂O was initially achieved as a fine chemical example over Pd(NO₃)₂/CeO₂-ZrO₂, and the target saturated alcohol (3-phenylpropan-1-ol) was obtained as the anti-Markovnikov selective product from a “one-pot” process using H₂ as the reductant. The Pd(NO₃)₂/CeO₂-ZrO₂ was characterized by HAADF-STEM, XRD and X-ray absorption fine structure (XAFS) analyses, indicating that the molecular Pd(NO₃)₂ is probably deposited as it is on the support, which likely plays an important role to promote this reaction. In the second part, Pd(NO₃)₂/CeO₂-ZrO₂ and other supported Pd catalysts were applied for the transformation of 1,3-butadiene into 2-butene-1,4-diol in a batch reactor. Besides, butane-1,4-diol, which is an important industrial material, was efficiently produced by the simple hydrogenation of 2-butene-1,4-diol in a “one-pot” manner. Significantly, the development of the reaction catalyzed by supported Pd in a gas flow reactor bestows great potential to further industrial applications. Additionally, the adsorption structure of 1,3-butadiene on Pd(111) was confirmed as the s-trans form by infrared reflection absorption spectroscopy (IRAS) measurements. The change in the electronic states of surface Pd atoms upon oxygen adsorption was observed by X-ray photoelectron spectroscopy (XPS).

DOI： 10.1016/j.apcatb.2019.01.031

Language：Others   Publishing type：Research paper (scientific journal)  

© 2019 Elsevier Inc. Palladium (Pd) clusters on zirconia (ZrO2) and single Pd atoms on ceria (CeO2) exhibited high catalytic activity and selectivity for decarbonylation of furfural to furan without additives in the liquid phase. To study the active size of Pd and changes in chemical states or structures during the reaction, in-situ X-ray absorption fine structure (XAFS) measurements were conducted. The size of Pd clusters consisting of less than 10 Pd atoms was maintained on ZrO2 during the reaction. In contrast, single Pd atoms were aggregated during heating and only Pd clusters consisting of 13 atoms were present after the reaction. According to the in-situ XAFS results, the size of Pd particles did not gradually increase to Pd13 clusters. Instead, Pd13 clusters were partly formed from the beginning of the reaction, and the proportion of Pd13 clusters increased with time while keeping the size of Pd13 clusters. This result suggests that a single Pd atom is inactive, but Pd clusters are active for decarbonylation. Ab-initio calculation revealed that ZrO2 (1 1 1) surface had lower adsorption and migration energies than CeO2 (1 1 1), implying that Pd was easily diffused on the surface and stabilized as small Pd clusters.

DOI： 10.1016/j.jcat.2019.04.041

Language：English   Publishing type：Research paper (scientific journal)  

Controllable methane oxidation directly into value-added products under mild conditions remains a challenge. Herein, an active Fe/MOR catalyst was synthesized via simple solid-state ion exchange, and its activity in the selective oxidation of methane with H₂O₂ in the aqueous phase was intensively investigated. The octahedral dimeric Fe³⁺ species [Fe₂(μ-O)₂] in the extra framework was confirmed as the initial active site by X-ray photoelectron spectroscopy, X-ray absorption near-edge structure and extended X-ray absorption fine structure, UV-vis diffuse-reflectance spectroscopy, and high-angle annular dark-field scanning transmission electron microscopy in combination with DFT calculations. The DFT calculations indicated that methanol formation via methyl peroxide (CH₃OOH∗) on [Fe₂(μ-OH)₂O₂] is the most favorable pathway compared to the direct formation of methanol via CH₃O∗. The formed CH₃OH is easily further oxidized by hydroxyl radicals (OH) resulting in non-selective methane oxidation. In contrast, the Fe/MOR catalyst could lead to a high methanol selectivity of 71.3% in the presence of homogeneous Cu²⁺ precursor, which efficiently suppressed the over-oxidation of methanol, and a high formic acid selectivity up to 81-82% at a slightly higher reaction temperature by mildly shifting the oxidation of methanol and formaldehyde to the target product.

DOI： 10.1039/c9cy01640f

Language：English   Publishing type：Research paper (scientific journal)  

Controllable methane oxidation directly into value-added products under mild conditions remains a challenge. Herein, an active Fe/MOR catalyst was synthesized via simple solid-state ion exchange, and its activity in the selective oxidation of methane with H₂O₂ in the aqueous phase was intensively investigated. The octahedral dimeric Fe³⁺ species [Fe₂(μ-O)₂] in the extra framework was confirmed as the initial active site by X-ray photoelectron spectroscopy, X-ray absorption near-edge structure and extended X-ray absorption fine structure, UV-vis diffuse-reflectance spectroscopy, and high-angle annular dark-field scanning transmission electron microscopy in combination with DFT calculations. The DFT calculations indicated that methanol formation via methyl peroxide (CH₃OOH∗) on [Fe₂(μ-OH)₂O₂] is the most favorable pathway compared to the direct formation of methanol via CH₃O∗. The formed CH₃OH is easily further oxidized by hydroxyl radicals (OH) resulting in non-selective methane oxidation. In contrast, the Fe/MOR catalyst could lead to a high methanol selectivity of 71.3% in the presence of homogeneous Cu²⁺ precursor, which efficiently suppressed the over-oxidation of methanol, and a high formic acid selectivity up to 81-82% at a slightly higher reaction temperature by mildly shifting the oxidation of methanol and formaldehyde to the target product.

DOI： 10.1039/c9cy01640f

Language：English   Publishing type：Research paper (scientific journal)  

Language：English   Publishing type：Research paper (scientific journal)  

Language：English   Publishing type：Research paper (scientific journal)  

Gold (Au) nanoparticles (NPs) supported on SiO₂ (Au/SiO₂) were prepared by a practical impregnation method and applied as an adsorbent for 1,3-dimethyltrisulfane (DMTS), which is responsible for an unpleasant odour in drinks, especially Japanese sake. Compared with a conventional adsorbent, activated carbon, Au/SiO₂ selectively reduced the DMTS concentration in Japanese sake without decreasing the concentrations of other aromatic components. DFT calculations revealed that the selective adsorption of DMTS occurred through the formation of a stable intermediate. The size of the supported Au NPs was controlled by the preparation conditions and determined from TEM observations and XRD measurements, and the size was ranged from 2.4 nm to 30 nm. Au/SiO₂ having Au NPs with a diameter of 2.4 nm adsorbed DMTS the most efficiently. Smaller Au NPs showed better DMTS adsorption capabilities because larger amounts of Au atoms were exposed on their surfaces in the size range of this study. Langmuir-type monolayer adsorption and one-to-one binding of Au–S are proposed to occur based on an adsorption isotherm experiment. Even though significant differences of the fruity aroma score were not observed in the sensory evaluation between Au/SiO₂ and activated carbon for this less aromatic Japanese sake, Au/SiO₂ selectively decreased the DMTS concentration in the instrumental analysis.

DOI： 10.1038/s41598-018-34217-w

Language：English   Publishing type：Research paper (scientific journal)  

We investigated the adsorption and thermal reactivity of dimethyl trisulfide (DMTS, CH₃SSSCH₃) on a Au(111) single-crystal surface. X-ray photoelectron spectroscopy results indicated that at exposure temperatures of 100–300 K, DMTS dissociatively adsorbed as CH₃S and CH₃SS. That the dissociative adsorption rate was independent of exposure temperature suggested that DMTS dissociation on Au proceeded without an energy barrier at >100 K. In contrast, the thermal reactions of the adsorbed CH₃S and CH₃SS varied strongly with formation temperature. Specifically, after CH₃S and CH₃SS formed on Au(111) at 100 K, increasing the temperature resulted in associative desorption of CH₃S as dimethyl disulfide (CH₃SSCH₃) and coupling reaction of CH₃SS to ethane and atomic sulfur. In contrast, after CH₃S and CH₃SS formed at 150 K, increasing the temperature resulted not only in these two reactions but also in production of dimethyl disulfide and atomic sulfur by reaction between CH₃S and CH₃SS. At formation temperatures of 200 and 300 K, the only reaction observed was that between CH₃S and CH₃SS. These results suggest that the surface structure of the adsorbed species formed by DMTS dissociation on Au(111) depended on formation temperature. Specifically, at 100 K, dissociation of DMTS resulted in formation of CH₃S and CH₃SS islands on the Au(111) surface, whereas the two species were randomly adsorbed at higher formation temperatures.

DOI： 10.1016/j.susc.2018.07.012

Language：English   Publishing type：Research paper (scientific journal)  

Asymmetric base hydrolysis of α-chiral esters with synthetic small-molecule catalysts is described. Quaternary ammonium salts derived from quinine were used as chiral phase-transfer catalysts to promote the base hydrolysis of N-protected amino acid hexafluoroisopropyl esters in a CHCl₃/NaOH (aq) via dynamic kinetic resolution, providing the corresponding products in moderate to good yields (up to 99%) with up to 96:4 er. Experimental and computational mechanistic studies using DFT calculation and pseudotransition state (pseudo-TS) conformational search afforded a TS model accounting for the origin of the stereoselectivity. The model suggested π-stacking and H-bonding interactions play essential roles in stabilizing the TS structures.

DOI： 10.1021/acscatal.8b00693

Language：Japanese   Publishing type：Research paper (scientific journal)  

Language：Japanese   Publishing type：Research paper (scientific journal)  

Language：Japanese   Publishing type：Research paper (scientific journal)  

Language：Japanese   Publishing type：Research paper (scientific journal)  

Language：Japanese   Publishing type：Research paper (scientific journal)  

Language：Japanese   Publishing type：Research paper (scientific journal)  

Direct C–H/C–H bond coupling of dimethyl phthalate was successfully performed over supported gold nanoparticle catalysts. Gold on reducible metal oxides, such as Co3O4, and on inert oxides having oxygen releasing capacity, such as ZrO2, showed the highest catalytic activity for the production of biphenyl tetracarboxylate using O2 as the sole oxidant. Supported Pd(OH)2 also catalyzed the reaction, but the catalytic activity was much inferior to that of Au. Moreover, Au catalysts exhibited excellent regioselectivity for the synthesis of valuable 3,3’,4,4’-tetrasubstituted biphenyls by coupling with each other at the m-position without the need for additional ligands. Gold catalysts also promoted the oxidative homocoupling of arenes including o-xylene to give symmetrical biaryls with high regioselectivity. X-ray absorption fine structure measurements revealed that the catalytically active species was Au0 and that the lattice oxygen of Co3O4 played an important role in the Au-catalyzed oxidative coupling. The results of the kinetic studies were consistent with an electrophilic aromatic substitution pathway. Regioselectivity is not controlled by directing groups or the electronic character of the substituents, but by steric hindrance, suggesting that gold nanoparticles not only catalyze the oxidative coupling but also act as bulky ligands to control regioselectivity.

Language：Japanese   Publishing type：Research paper (scientific journal)  

Language：English   Publishing type：Research paper (scientific journal)  

Transformation of cyclohexanones to phenols and aryl ethers over supported Pd catalysts using molecular oxygen as the sole oxidant is developed. Several metal oxide supported Pd catalysts were used to activate the C-H bond in cyclohexanones to produce cyclohexenones and phenols through oxidation. Although the selectivity of cyclohexenones was difficult to control, phenols were obtained in excellent yield with a broad substrate scope. A novel catalytic system, using ZrO2 supported Pd(OH)2, was proposed for the synthesis of aryl ethers, and the products were obtained in moderate to excellent yields. Orthoesters, such as trimethyl orthoformate (TMOF), triethyl orthoformate (TEOF), and triisopropyl orthoformate (TIPOF), enabled nucleophilic addition and elimination after activation of cyclohexanones over a Pd catalyst to produce the corresponding aryl ethers. TIPOF was also used as the dehydrating reagent to promote the reaction of cyclohexanones with alcohols for the preparation of versatile aryl ethers.

DOI： 10.1039/c4qo00354c

Language：Japanese   Publishing type：Research paper (scientific journal)  

Language：Japanese   Publishing type：Research paper (scientific journal)  

Language：Japanese  

Asymmetric Basic Hydrolysis with Chiral Quaternary Ammonium Salts

Language：Japanese   Publishing type：Research paper (scientific journal)  

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DOI： 10.1016/j.apcatb.2013.12.051

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DOI： 10.1016/j.apcata.2013.09.043

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DOI： 10.1039/C3CY00336A

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DOI： org/10.1016/j.jcat.2013.07.027.

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DOI： 10.1021/jp403104

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DOI： 0.1016/j.apcata.2013.03.042

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DOI： 10.1016/B978-0-08-095167-6.00520-6

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2009, 11, 5510-5513.

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Hydrolytic deallylation of N-allyl amides to give amides and propanal can be achieved with Pd-II catalysts. The optimized catalyst consists of Pd(OCOCF3)(2) and 1,3-bis(diphenylphosphanyl)propane (DPPP). Several kinds of open-chain N-allyl amides and N-allyl lactams undergo hydrolytic deallylation to give the corresponding amides and lactams in good to high yield. A mechanism which includes isomerization to enamides and subsequent hydrolysis is proposed. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

DOI： 10.1002/ejoc.200800771

Language：English   Publishing type：Research paper (scientific journal)  

Language：English  

Language：English   Publishing type：Research paper (scientific journal)  

Kinetic resolution of phosphoryl and sulfonyl esters of 1,1'-bi-2-naphthol has been achieved via the Pd-catalyzed alcoholysis of their vinyl ethers. The highest k(rel) value reached 36.8 with substrate 3c. and (R)-3c 99.0% ee was obtained in 43% isolated yield. (C) 2008 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetasy.2008.06.034

Language：English   Publishing type：Research paper (scientific journal)  

Language：English   Publishing type：Research paper (scientific journal)  

Au(I) complexes-catalyzed transfer vinylation of alcohols and carboxylic acids has been achieved. The catalyst system consists of 2 mol % AuClPPh(3) and 2 mol % AgOAc. Primary alcohols and secondary alcohols were converted into corresponding vinyl ethers in good yield (64-93%); however, tertiary alcohols showed poor reactivities. Carboxylic acids were also transformed into corresponding vinyl esters in good yield (78-96%). (C) 2008 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2008.04.037

Language：English   Publishing type：Research paper (scientific journal)  

Language：English   Publishing type：Research paper (scientific journal)  

Oxidation of cyclohexanones into conjugated enones with molecular oxygen as oxidant was achieved by palladium catalysts. A catalyst system consists of I mol % Pd(OCOCF3)(2) and 5,5'-dimethyl-2,2'-bipyridine accomplished maximum 84% yield for the oxidation of cyclohexanone and 51-78% yields for 4-SLibstituted-cyclohexanones. (C) 2007 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2007.07.181

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The aim of this study was to evaluate the effect of feeding yoghurt, prepared with Lactobacillus delbrueckii subsp. bulgaricus strain 2038, on indigenous lactobacilli in the pig cecum. Three female pigs fistulated at the cecum were,fed 2 50 g of this yoghurt that contained over 10(11) colony-forming units of L. delbrueckii subsp. bulgaricus strain 2038 with their daily meal for 2 wk. The relative abundance and the composition of cecal lactobacilli was monitored by analysis of bacterial 16S rDNA with real time PCR and amplified bacterial rDNA restriction analysis using Lactobacillus-group specific primers, respectively, for 2 wk prior to, at the end of 2 wk of and 2 wk after the administration of this yoghurt. The relative abundance of lactobacilli was significantly increased by feeding yoghurt (p < 0.01.), although the bacterial J6S rDNA matching L. delbrueckii subsp. bulgaricus strain 2038 was not detected by amplified bacterial rDNA restriction analysis during this study. The number of operational taxonomic units (OTUs) detected was increased with feeding of the yoghurt in all pigs. At the same time, the estimated cell number of each OTU was increased with feeding of the yoghurt. It is demonstrated that continuous consumption of the probiotic lactobacilli will stimulate the growth of some indigenous lactobacilli and alter the composition of the lactobacilli.

DOI： 10.3177/jnsv.53.82

Language：English   Publishing type：Research paper (scientific journal)  

Language：English   Publishing type：Research paper (scientific journal)  

Optically pure phosphoroselenoyl chloride was reacted with racemic amines to give phosphoroselenoic amides as two diastereomeric mixtures in high yields. The diastereomeric mixtures were separated by fractional recrystallization or by chromatography. Extrusion of the selenium atom from the separated amides led to diastercomerically pure phosphoramidites. The ability of the obtained amidites to act as optically active ligands was tested in the hydrogenation of an imine.

DOI： 10.1246/cl.2006.1424

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BINAP-Ru catalyzed hydrogenation of configurationally labile α-amido β-keto phosphonic esters gives the (R,R)- or (S,S)-α-amido β-hydroxy phosphonic esters in a highly enantio- and diastereoselective manner.

DOI： 10.1016/00404-0399(50)11355-

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Event date： 2022.7

Language：Japanese  

Venue：福岡   Country：Japan  

Event date： 2022.6

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：京都   Country：Japan  

Event date： 2022.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：オンライン   Country：Japan  

Event date： 2022.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：オンライン   Country：Japan  

Event date： 2022.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：オンライン   Country：Japan  

Event date： 2022.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：オンライン   Country：Japan  

Event date： 2022.3

Language：Japanese  

Venue：東京   Country：Japan  

Event date： 2022.1

Language：Japanese  

Venue：熊本   Country：Japan  

Event date： 2021.9

Language：Japanese  

Venue：オンライン   Country：Japan  

Event date： 2021.9

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：オンライン   Country：Japan  

Event date： 2021.9

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：オンライン   Country：Japan  

Event date： 2021.9

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：オンライン   Country：Japan  

Event date： 2021.9

Language：Japanese  

Venue：オンライン   Country：Japan  

Event date： 2021.8

Language：Japanese  

Venue：WEB   Country：Japan  

Event date： 2021.7

Language：Japanese  

Venue：WEB   Country：Japan  

Event date： 2021.7

Language：Japanese  

Venue：WEB   Country：Japan  

Event date： 2021.7

Language：Japanese  

Venue：WEB   Country：Japan  

Event date： 2021.7

Language：Japanese  

Venue：WEB   Country：Japan  

Event date： 2021.3

Language：Japanese   Presentation type：Oral presentation (general)  

Country：Japan  

Event date： 2021.3

Language：Japanese  

Country：Japan  

Event date： 2021.3

Language：Japanese  

Country：Japan  

Event date： 2020.10

Language：Japanese  

Venue：オンライン   Country：Japan  

Event date： 2020.10

Language：Japanese  

Venue：オンライン   Country：Japan  

Event date： 2020.10

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：オンライン   Country：Japan  

Event date： 2020.10

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：オンライン   Country：Japan  

Event date： 2020.10

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：オンライン   Country：Japan  

Event date： 2020.10

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：オンライン   Country：Japan  

Event date： 2020.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：千葉   Country：Japan  

Event date： 2020.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：千葉   Country：Japan  

Event date： 2020.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：千葉   Country：Japan  

Event date： 2020.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：千葉   Country：Japan  

Event date： 2019.12

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：筑波   Country：Japan  

Event date： 2019.11

Language：Japanese  

Venue：名古屋   Country：Japan  

Event date： 2019.11

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：京都   Country：Japan  

Event date： 2019.11 - 2019.12

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：福岡   Country：Japan  

Event date： 2019.9

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：神戸   Country：Japan  

Event date： 2019.9

Language：Japanese  

Venue：神戸   Country：Japan  

Event date： 2019.9

Language：Japanese  

Venue：長崎   Country：Japan  

Event date： 2019.9

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：長崎   Country：Japan  

Event date： 2019.9

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：長崎   Country：Japan  

Event date： 2019.9

Language：Japanese  

Venue：長崎   Country：Japan  

Event date： 2019.9

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：福岡   Country：Japan  

Event date： 2019.7 - 2019.12

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：北九州   Country：Japan  

Event date： 2019.7

Language：Japanese  

Venue：北九州   Country：Japan  

Event date： 2019.7

Language：Japanese  

Venue：北九州   Country：Japan  

Event date： 2019.7

Language：Japanese  

Venue：北九州   Country：Japan  

Event date： 2019.7

Language：Japanese  

Venue：北九州   Country：Japan  

Event date： 2019.7

Language：Japanese  

Venue：北九州   Country：Japan  

Event date： 2019.6

Language：Japanese  

Venue：熊本   Country：Japan  

Event date： 2019.6

Language：Japanese  

Venue：熊本   Country：Japan  

Event date： 2019.6

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：Frejus   Country：France  

Event date： 2019.5

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：台湾   Country：Taiwan, Province of China  

Event date： 2019.5

Language：Japanese  

Venue：福岡   Country：Japan  

Event date： 2019.4

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：京都   Country：Japan  

Event date： 2019.4

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：大阪   Country：Japan  

Event date： 2019.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：京都   Country：Japan  

Event date： 2019.3

Language：Japanese  

Venue：大阪   Country：Japan  

Event date： 2019.3

Language：Japanese  

Venue：神戸   Country：Japan  

Event date： 2019.3

Language：Japanese   Presentation type：Oral presentation (general)  

Country：Japan  

Event date： 2019.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：神戸   Country：Japan  

Event date： 2019.3

Language：Japanese   Presentation type：Public lecture, seminar, tutorial, course, or other speech  

Venue：神戸   Country：Japan  

Event date： 2019.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：神戸   Country：Japan  

Event date： 2019.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：東京   Country：Japan  

Event date： 2019.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：Singapore   Country：Singapore  

Event date： 2018.11

Language：Japanese  

Venue：福岡   Country：Japan  

Event date： 2018.11

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：大阪   Country：Japan  

Event date： 2018.10

Language：Japanese  

Venue：東京   Country：Japan  

Event date： 2018.9

Language：Japanese  

Venue：北海道   Country：Japan  

Event date： 2018.9

Language：Japanese  

Venue：北海道   Country：Japan  

Event date： 2018.9

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：北海道   Country：Japan  

Event date： 2018.9

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：北海道   Country：Japan  

Event date： 2018.9

Language：Japanese  

Venue：北海道   Country：Japan  

Event date： 2018.9

Language：Japanese  

Venue：北海道   Country：Japan  

Event date： 2018.9

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：北海道   Country：Japan  

Event date： 2018.9

Language：Japanese  

Venue：福岡   Country：Japan  

Event date： 2018.8

Language：Japanese  

Venue：佐賀   Country：Japan  

Event date： 2018.8

Language：Japanese  

Venue：佐賀   Country：Japan  

Event date： 2018.7

Language：Japanese  

Venue：Krakow   Country：Poland  

Event date： 2018.7

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：Paris   Country：France  

Event date： 2018.7

Language：Japanese  

Venue：Paris   Country：France  

Event date： 2018.7

Language：Japanese  

Venue：Paris   Country：France  

Event date： 2018.7

Language：Japanese  

Venue：Paris   Country：France  

Event date： 2018.6

Language：Japanese  

Venue：北九州   Country：Japan  

Event date： 2018.6

Language：Japanese  

Venue：北九州   Country：Japan  

Event date： 2018.6

Language：Japanese  

Venue：北九州   Country：Japan  

Event date： 2018.6

Language：Japanese  

Venue：北九州   Country：Japan  

Event date： 2018.6

Language：Japanese  

Venue：北海道   Country：Japan  

Event date： 2018.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：東京   Country：Japan  

Event date： 2018.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：千葉   Country：Japan  

Event date： 2018.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：千葉   Country：Japan  

Event date： 2018.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：千葉   Country：Japan  

Event date： 2018.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：千葉   Country：Japan  

Event date： 2017.12

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：東京   Country：Japan  

Event date： 2017.11 - 2017.12

Language：Japanese  

Venue：宮城   Country：Japan  

Event date： 2017.11 - 2017.12

Language：Japanese  

Venue：宮城   Country：Japan  

Event date： 2017.11

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：福岡   Country：Japan  

Event date： 2017.10 - 2017.11

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：東京   Country：Japan  

Event date： 2017.10

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：東京   Country：Japan  

Event date： 2017.9

Language：Japanese  

Venue：愛媛   Country：Japan  

Event date： 2017.9

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：愛媛   Country：Japan  

Event date： 2017.9

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：愛媛   Country：Japan  

Event date： 2017.8 - 2017.9

Language：Japanese  

Venue：神奈川   Country：Japan  

Event date： 2017.7

Language：Japanese  

Venue：北九州   Country：Japan  

Event date： 2017.7

Language：Japanese  

Venue：北九州   Country：Japan  

Event date： 2017.7

Language：Japanese  

Venue：北九州   Country：Japan  

Event date： 2017.7

Language：Japanese  

Venue：北九州   Country：Japan  

Event date： 2017.6

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

Venue：岡山   Country：Japan  

Event date： 2017.6

Language：Japanese  

Venue：岡山   Country：Japan  

Event date： 2017.6

Language：Japanese  

Venue：福岡   Country：Japan  

Event date： 2017.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：東京   Country：Japan  

Event date： 2017.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：神奈川   Country：Japan  

Event date： 2017.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：神奈川   Country：Japan  

Event date： 2017.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：神奈川   Country：Japan  

Event date： 2017.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：神奈川   Country：Japan  

Event date： 2017.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：神奈川   Country：Japan  

Event date： 2017.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：神奈川   Country：Japan  

Event date： 2016.11 - 2016.12

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：千葉   Country：Japan  

Event date： 2016.11

Language：Japanese  

Venue：東京   Country：Japan  

Event date： 2016.11

Language：Japanese  

Venue：東京   Country：Japan  

Event date： 2016.11

Language：Japanese  

Venue：東京   Country：Japan  

Event date： 2016.11

Language：Japanese  

Venue：東京   Country：Japan  

Event date： 2016.10

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：ハワイ   Country：United States  

Event date： 2016.8

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：千葉   Country：Japan  

Event date： 2016.8

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：福岡   Country：Japan  

Event date： 2016.8

Language：Japanese  

Venue：福岡   Country：Japan  

Event date： 2016.8

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：福岡   Country：Japan  

Event date： 2016.7

Language：Japanese  

Venue：北九州   Country：Japan  

Event date： 2016.7

Language：Japanese  

Venue：北九州   Country：Japan  

Event date： 2016.7

Language：Japanese  

Venue：北九州   Country：Japan  

Event date： 2016.7

Language：Japanese  

Venue：北九州   Country：Japan  

Event date： 2016.7

Language：Japanese  

Venue：北九州   Country：Japan  

Event date： 2016.7

Language：Japanese  

Venue：北九州   Country：Japan  

Event date： 2016.5

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：千葉   Country：Japan  

Event date： 2016.5

Language：English   Presentation type：Oral presentation (general)  

Venue：福岡   Country：Japan  

Event date： 2016.5

Language：Japanese  

Venue：Frejus   Country：France  

Event date： 2016.4

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：福岡   Country：Japan  

Event date： 2016.4

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：福岡   Country：Japan  

Event date： 2016.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：京都   Country：Japan  

Event date： 2016.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：京都   Country：Japan  

Event date： 2016.3

Language：Japanese   Presentation type：Oral presentation (general)  

Country：Japan  

Event date： 2016.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：京都   Country：Japan  

Event date： 2016.3

Language：Japanese  

Venue：京都   Country：Japan  

Event date： 2016.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：京都   Country：Japan  

Event date： 2016.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：京都   Country：Japan  

Event date： 2016.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：京都   Country：Japan  

Event date： 2016.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：京都   Country：Japan  

Event date： 2016.3

Language：Japanese  

Venue：京都   Country：Japan  

Event date： 2016.3

Language：Japanese  

Venue：京都   Country：Japan  

Event date： 2016.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：京都   Country：Japan  

Event date： 2016.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：京都   Country：Japan  

Event date： 2016.3

Language：Japanese  

Venue：大阪   Country：Japan  

Event date： 2016.3

Language：Japanese  

Venue：大阪   Country：Japan  

Event date： 2016.3

Language：Japanese  

Venue：大阪   Country：Japan  

Event date： 2016.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：大阪   Country：Japan  

Event date： 2016.1

Language：Japanese  

Venue：名古屋   Country：Japan  

Event date： 2016.1

Language：Japanese  

Venue：大阪   Country：Japan  

Event date： 2015.12

Language：Japanese  

Venue：Hawaii   Country：United States  

Event date： 2015.12

Language：English  

Venue：Hawaii   Country：United States  

Event date： 2015.12

Language：English  

Venue：Hawaii   Country：United States  

Event date： 2015.12

Language：English  

Venue：Hawaii   Country：United States  

Event date： 2015.12

Language：Japanese  

Venue：Hawaii   Country：United States  

Event date： 2015.12

Language：Japanese  

Venue：Hawaii   Country：United States  

Event date： 2015.12

Language：English  

Venue：Hawaii   Country：United States  

Event date： 2015.12

Language：English  

Venue：Hawaii   Country：United States  

Event date： 2015.12

Language：English  

Venue：Hawaii   Country：United States  

Event date： 2015.12

Language：Japanese  

Venue：Hawaii   Country：United States  

Event date： 2015.12

Language：English  

Venue：Hawaii   Country：United States  

Event date： 2015.11

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：岡山   Country：Japan  

Event date： 2015.11

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：長野   Country：Japan  

Event date： 2015.10

Language：Japanese  

Venue：東京   Country：Japan  

Event date： 2015.9

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：China   Country：Japan