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Development of Regioselective C-H Trifluoromethylation

Research Project

Project/Area Number 16K13946
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Organic chemistry
Research InstitutionKyushu University

Principal Investigator

Kuninobu Yoichiro  九州大学, 先導物質化学研究所, 教授 (40372685)

Project Period (FY) 2016-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥3,640,000 (Direct Cost: ¥2,800,000、Indirect Cost: ¥840,000)
Fiscal Year 2017: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2016: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Keywordsトリフルオロメチル化 / 位置選択的 / ヘテロ芳香族化合物 / Lewis酸-塩基相互作用 / Lewis酸 / 銅触媒 / トリフルオロメチルアニオン / ヘテロ芳香環 / 芳香環 / フッ素官能基
Outline of Final Research Achievements

We succeeded in the development of the first 4-position-selective C-H trifluoromethylation of six-membered heteroaromatic compounds by electrophilically activating the six-membered heteroaromatic rings and sterically protecting the 2-position of the heteroaromatic rings.We developed copper-catalyzed 5-position-selective C-H trifluoromethylation of N-(8-quinolynyl)pivalamides. In addition, we succeeded in the inprovement of previously reported 2-position-selective C-H trifluoromethylation of six-membered heteroaromatic compounds. By using this reaction, a trifluoromethyl group can be introduced into the 2-position of quinoline derivatives in short reaction steps efficiently.

Report

(3 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Research-status Report
  • Research Products

    (15 results)

All 2018 2017 2016 Other

All Journal Article (3 results) (of which Peer Reviewed: 3 results,  Acknowledgement Compliant: 1 results) Presentation (8 results) (of which Int'l Joint Research: 1 results,  Invited: 8 results) Book (1 results) Remarks (3 results)

  • [Journal Article] 2-Position-Selective C?H Perfluoroalkylation of Quinoline Derivatives2018

    • Author(s)
      Shirai Takahiro、Kanai Motomu、Kuninobu Yoichiro
    • Journal Title

      Organic Letters

      Volume: 20 Issue: 6 Pages: 1593-1596

    • DOI

      10.1021/acs.orglett.8b00339

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 4-Position-Selective C-H Perfluoroalkylation and Perfluoroarylation of Six-Membered Heteroaromatic Compounds2016

    • Author(s)
      Masahiro Nagase, Yoichiro Kuninobu, Motomu Kanai
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 138 Issue: 19 Pages: 6103-6106

    • DOI

      10.1021/jacs.6b01753

    • Related Report
      2016 Research-status Report
    • Peer Reviewed
  • [Journal Article] 5-Position-selective C-H Trifluoromethylation of 8-Aminoquinoline Derivatives.2016

    • Author(s)
      Yoichiro Kuninobu, Mitsumi Nishi, Motomu Kanai
    • Journal Title

      Org. Biomol. Chem.

      Volume: 14 Issue: 34 Pages: 8092-8100

    • DOI

      10.1039/c6ob01325b

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] Regioselective C-H Trifluoromethylation of 6-Membered Heteroaromatic Compounds2018

    • Author(s)
      Yoichiro Kuninobu
    • Organizer
      International Congress on Pure & Applied Chemistry (ICPAC 2018), Cambodia
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 位置選択的なトリフルオロメチル化反応の開発2017

    • Author(s)
      國信 洋一郎
    • Organizer
      第14回フッ素相模セミナー
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 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2017

    • Author(s)
      國信 洋一郎
    • Organizer
      第29回若手研究者のためのセミナー
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] Development of C-H Bond Transformations Directed Towards the Synthesis of Organic Functional Molecules2017

    • Author(s)
      Yoichiro Kuninobu
    • Organizer
      Lecture at Tsinghua University, China
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] Development of C-H Bond Transformations Directed Towards the Synthesis of Organic Functional Molecules2017

    • Author(s)
      Yoichiro Kuninobu
    • Organizer
      Lecture at Peking University, China
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] Development of C-H Bond Transformations Directed Towards the Synthesis of Organic Functional Molecules2017

    • Author(s)
      Yoichiro Kuninobu
    • Organizer
      Lecture at Institute of Chemistry, Chinese Academy of Sciences, China
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 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2017

    • Author(s)
      國信 洋一郎
    • Organizer
      第4回次世代の有機化学・広島シンポジウム
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 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2017

    • Author(s)
      國信 洋一郎
    • Organizer
      第44回有機典型元素化学討論会
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Book] 有機合成化学協会誌2016

    • Author(s)
      Yoichiro Kuninobu
    • Total Pages
      11
    • Publisher
      有機合成化学協会
    • Related Report
      2016 Research-status Report
  • [Remarks] 國信研究室HP(日本語)

    • URL

      http://kuninobu-lab.cm.kyushu-u.ac.jp/

    • Related Report
      2017 Annual Research Report
  • [Remarks] 國信研究室HP(英語)

    • URL

      http://kuninobu-lab-english.cm.kyushu-u.ac.jp/

    • Related Report
      2017 Annual Research Report
  • [Remarks] 國信研究室HP

    • URL

      http://kuninobu-lab.cm.kyushu-u.ac.jp/

    • Related Report
      2016 Research-status Report

URL: 

Published: 2016-04-21   Modified: 2019-03-29  

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