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Takayuki IWATA Last modified date:2022.06.16



Graduate School
Undergraduate School


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Homepage
https://kyushu-u.pure.elsevier.com/en/persons/takayuki-iwata
 Reseacher Profiling Tool Kyushu University Pure
https://shindo-kano-lab.weebly.com/
Phone
092-583-7805
Fax
092-583-7803
Academic Degree
Ph. D.
Country of degree conferring institution (Overseas)
No
Field of Specialization
Synthetic organic chemistry
Total Priod of education and research career in the foreign country
01years00months
Outline Activities
My research is focused on 1) development of new organic reactions, 2) synthesis of biological active compounds and 3) synthesis of new aromatic compounds based on triptycenes.
Research
Research Interests
  • My research involves 1) development of novel organic reactions, 2) synthesis of biological active compounds including natural products and 3) synthesis of functional molecules based on triptycenes.
    keyword : organic synthesis, new reaction development, iptycene
    2016.04.
Academic Activities
Reports
1. Mitsuru Shindo  ∗ , Takayuki Iwata , Cycloaddition Initiated by Ynolates: High-Energy Dianion Equivalents as a Molecular Glue, Synlett 2022; 33(06): 531-545, 2021.11.
2. Takayuki Iwata, Mitsuru Shindo, Synthesis of 1,8,13-substituted triptycenes, Chem. Lett. 50, 39 (2021)., 2021.06.
Papers
1. Takayuki Iwata∗ , Mizuki Hyodo , Takumi Fujiwara , Ryusei Kawano , Leah Kuhn , Igor V. Alabugin , Mitsuru Shindo, 3-Trifluoromethylbenzyne: Precise Orientation in Cycloaddition Reaction Enabled Regioselective Synthesis of Trifluoromethylated Triptycenes, Synthesis, 2022.04, The first regioselective addition reactions to 3-trifluoromethylbenzyne are reported. Triple cycloaddition of ynolates to the benzyne provided 1,8,13-tris(trifluoromethyl)triptycenes with high regioselectivity. 1-Trifluoromethyltriptycenes were regioselectively obtained by the Diels–Alder reaction of anthranoxides with the benzyne. These selectivities are attributed to the electron-acceptor nature of the trifluoromethyl group on the benzyne..
2. Mitsuru Shindo, Takayuki Iwata , Cycloaddition Initiated by Ynolates: High-Energy Dianion Equivalents as a Molecular Glue, Synlett , 10.1055/s-0040-1719857, 33, 06, 531-545, 2021.11, In this paper, ynolate-initiated cycloaddition (annulation) to form a range of carbocycles and heterocycles is described. Ynolates consist of a ketene anion equivalent, which contains both nucleophilic and electrophilic moieties, and a carbodianion equivalent that achieves double addition. Hence, in addition to the usual [n+2] cycloaddition, ynolates can perform formal [n+1]-type annulations. Their high-energy performance has been demonstrated by their triple addition to arynes to generate triptycenes, in which the C–C triple bond of ynolates is cleaved. The synthetic applications of these methods, including natural products synthesis, are also described..
3. T. Iwata, R. Kawano, T. Fukami, M. Shindo, Retro-Friedel-Crafts-Type Acidic Ring-Opening of Triptycenes: A New Synthetic Approach to Acenes, Chem. Euro. J., 10.1002/chem.202104160, 28, 12, e202104160, 2022.01, The triptycene scaffold has been ring-opened in a retro-Friedel-Crafts-type reaction under acidic conditions to give its corresponding anthrone product. 9-Hydroxytriptycenes and unsubstituted triptycene undergo ring-opening reaction under strongly acidic conditions, such as with TfOH. An investigation of the substitution effect has revealed that the electron-donating group on the arene moiety allows the reaction to proceed in the presence of a weaker acid, such as TFA. In addition, the reaction has been successfully applied toward the synthesis of tetracene..
4. T. Iwata, S. Kumagai, T. Yoshinaga, M. Hanada, Y. Shiota, K. Yoshizawa, M. Shindo, Quadruple Role of Pd Catalyst in Domino Reaction Involving Aryl to Alkyl 1,5-Pd Migration to Access 1,9-Bridged Triptycenes., Chem. Euro. J. accepted, 2021.06.
5. T. Iwata, T. Yoshinaga, M. Shindo, Flow synthesis of triptycene via triple cycloaddition of ynolate to benzyne, Synlett、31, 1903-1906 (2020), 2020.07.
6. S. Umezu, G. d. P. Gomes, T. Yoshinaga, M.Sakae, K. Matsumoto, T. Iwata, I. Alabugin, M. Shindo, Regioselective One-pot Synthesis of Triptycenes via Triple-Cycloadditions of Arynes to Ynolates, Angew. Chem. Int. Ed. 56, 1298-1302 (2017), 2016.12.
Presentations
1. Takayuki Iwata, Tatsuro Yoshinaga, Yusuke Maehata, Takumi Fujiwara, Mitsuru Shindo, Regioselective synthesis of 1,8,13-syn-substituted triptycenes using triple cycloaddition of ynolates to 3-silylbenzynes, Pacifichem 2021, 2021.12.
2. Construction of Molecular Spaces based on syn-Substituted Triptycenes
.
3. Takayuki Iwata, Satoshi Fujita, Taishi Tomiyama, Kenji Matsumoto, Masayo Hirao-Suzuki, Shuzo Takeda, Mitsuru Shindo , Asymmetric Total Synthesis, Stereochemical Stability and Cancer Cell Killing Effects of Stemona Alkaloids, The 99th CSJ Annual Meeting, 2019.03.
4. Takayuki Iwata, Tatusro Yoshinaga, Satoshi Umezu, Takumi Fujiwara,Mikei Sakae, Kenji Matsumoto, Mitsuru Shindo, Regioselective Synthesis of Substituted Triptycenes Using Ynolate-aryne Triplecycloadditions, IKCOC-14, 2018.11.
Membership in Academic Society
  • The society of synthetic organic chemistry, Japan
  • The chemical society of Japan