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New transformations building on thiyl radical catalysis

Research Project

Project/Area Number 15H03778
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionChiba University (2017-2018)
Kyoto University (2015-2016)

Principal Investigator

Hashimoto Takuya  千葉大学, 大学院理学研究院, 特任准教授 (20437198)

Project Period (FY) 2015-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥16,770,000 (Direct Cost: ¥12,900,000、Indirect Cost: ¥3,870,000)
Fiscal Year 2017: ¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2016: ¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2015: ¥7,930,000 (Direct Cost: ¥6,100,000、Indirect Cost: ¥1,830,000)
Keywordsラジカル反応 / 硫黄 / チイルラジカル / 触媒 / ラジカル / 均一系触媒
Outline of Final Research Achievements

One notable result is the [3 + 2] cyclization reaction of vinylaziridine and alkene realized for the first time by using bulky organic sulfur radical, and this work is published in a top chemistry journal, Angwandte Chemie International Edition. As for asymmetric synthesis catalyzed by thiyl radical, we succeeded in developing a new chiral scaffold that can perform cyclization reaction of vinylcyclopropane and alkene. Furthermore, in the carbon-carbon bond formation reaction accompanied by hydrogen atom transfer, we succeeded in developing the first catalytic reaction by thiyl radical.

Academic Significance and Societal Importance of the Research Achievements

有機合成化学は市販の物質を他の人類社会に有用な化学物質に変換する方法の科学であり、医薬品や化成品の開発や供給に不可欠な技術である。無数にある市販物質から特定の欲しい物質に変換するには、その分子変換手法も数多く必要であり、150年以上にわたり世界中の研究者がより効率的な分子変換法の開発に取り組んできた。その長い歴史の中でもラジカルと呼ばれる不安定化学種を利用した有機合成化学は、制御できない反応として有用物質合成法には使われてこなかった。本研究ではそのラジカル種を触媒的に発生させつつ、使える分子変換法として成立させることに寄与した。

Report

(4 results)
  • 2018 Final Research Report ( PDF )
  • 2017 Annual Research Report
  • 2016 Annual Research Report
  • 2015 Annual Research Report
  • Research Products

    (9 results)

All 2019 2017 2016 2015

All Journal Article (2 results) (of which Peer Reviewed: 2 results,  Acknowledgement Compliant: 1 results) Presentation (7 results) (of which Int'l Joint Research: 1 results,  Invited: 6 results)

  • [Journal Article] A Chiral Electrophilic Selenium Catalyst for Highly Enantioselective Oxidative Cyclization2016

    • Author(s)
      Yu Kawamata, Takuya Hashimoto, Keiji Maruoka
    • Journal Title

      Journal of the American Chemical Society

      Volume: n/a Issue: 16 Pages: 5206-5209

    • DOI

      10.1021/jacs.6b01462

    • Related Report
      2016 Annual Research Report 2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A Bulky Thiyl-Radical Catalyst for the [3+2] Cyclization of N-Tosyl Vinylaziridines and Alkenes2016

    • Author(s)
      T. Hashimoto, K. Takino, K. Hato, K. Maruoka
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 55 Issue: 28 Pages: 8081-8085

    • DOI

      10.1002/anie.201602723

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] 触媒・リガンドデザインで可能になる有機合成2019

    • Author(s)
      橋本卓也
    • Organizer
      有機金属部会H30年度第4回例会
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] Pursuit of New Catalyst Designs2019

    • Author(s)
      Takuya Hashimoto
    • Organizer
      KEIO International Symposium on Innovative Molecular Transformations
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 新しい分子触媒デザインの探求2017

    • Author(s)
      橋本卓也
    • Organizer
      東京農工大学 講演会
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] 新しい分子触媒デザインの探求2017

    • Author(s)
      橋本卓也
    • Organizer
      早稲田大学理工学術院 講演会
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] A Chiral Electrophilic Selenium Catalyst for Highly Enantioselective Oxidative Cyclization2016

    • Author(s)
      Y. Kawamata, T. Hashimoto, K. Maruoka
    • Organizer
      日本化学会 第96春季年会
    • Place of Presentation
      京田辺市
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] Pursuit of New Catalyst Designs2016

    • Author(s)
      Hashimoto, T.
    • Organizer
      ACT-C 不斉炭素‐炭素結合形成反応・若手ワークショップ
    • Place of Presentation
      東京都千代田区
    • Year and Date
      2016-03-05
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] Exploration of Untapped Functionalities in Organocatalysis2015

    • Author(s)
      Hashimoto, T.
    • Organizer
      Organic chemistry symposium Royal Society of Chemistry Roadshow
    • Place of Presentation
      京都市
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited

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Published: 2015-04-16   Modified: 2020-03-30  

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