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Asymmetric C-H bond functionalization using cobalt catalyst via ligand-directing group interaction

Research Project

Project/Area Number 15H05993
Research Category

Grant-in-Aid for Research Activity Start-up

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionHokkaido University

Principal Investigator

YOSHINO Tatsuhiko  北海道大学, 薬学研究院, 助教 (50756179)

Project Period (FY) 2015-08-28 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥2,990,000 (Direct Cost: ¥2,300,000、Indirect Cost: ¥690,000)
Fiscal Year 2016: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2015: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Keywords不斉触媒 / C-H活性化 / C-H官能基化 / キラルカルボン酸 / キラル対アニオン / C-H結合活性化 / コバルト触媒 / イリジウム触媒 / 炭素-水素結合活性化 / アリル化 / アルケニル化
Outline of Final Research Achievements

This project had intended to develop new catalysts for stereoselective and more efficient C-H bond functionalization reactions using interaction between the ligand and directing group. However, it was revealed that new chiral carboxylic acids and introduction of a chiral counter anion can effectively control the stereoselectivity of several reactions during the research. In addition, the scope of high-valent cobalt catalyzed reactions was successfully expanded, and C-H allylation of more general substrates using allyl alcohols, site-selective alkenylation, and trifluoromethylthiolation were achieved.

Report

(3 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Annual Research Report
  • Research Products

    (7 results)

All 2017 2016 2015

All Journal Article (3 results) (of which Peer Reviewed: 3 results,  Acknowledgement Compliant: 2 results) Presentation (4 results)

  • [Journal Article] Cp*CoIII-Catalyzed Dehydrative C-H Allylation of 6-Arylpurines and Aromatic Amides Using Allyl Alcohols in Fluorinated Alcohols2016

    • Author(s)
      Bunno, Y.; Murakami, N.; Suzuki, Y.; Kanai, M.; Yoshino, T.; Matsunaga, S.
    • Journal Title

      Org. Lett.

      Volume: 18 Issue: 9 Pages: 2216-2219

    • DOI

      10.1021/acs.orglett.6b00846

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Site- and Regioselective Monoalkenylation of Pyrroles with Alkynes via Cp*CoIII Catalysis2016

    • Author(s)
      Tanaka, R.; Ikemoto, H.; Kanai, M.; Yoshino, T.; Matsunaga, S.
    • Journal Title

      Org. Lett.

      Volume: 18 Issue: 21 Pages: 5732-5735

    • DOI

      10.1021/acs.orglett.6b02997

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Cp*CoIII-Catalyzed Site-Selective C-H Activation of Unsymmetrical O-Acyl Oximes: Synthesis of Multisubstituted Isoquinolines from Terminal and Internal Alkynes2015

    • Author(s)
      Bo Sun, Tatsuhiko Yoshino ,Motomu Kanai, Shigeki Matsunaga
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 54 Issue: 44 Pages: 12968-12972

    • DOI

      10.1002/anie.201507744

    • NAID

      120005853061

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Presentation] Cp*Co(III)-catalyzed C-H Bond Functionalization Reactions2017

    • Author(s)
      Tatsuhiko Yoshino, Youka Bunno, Ryo Tanaka, Hideya Ikemoto, Yudai Suzuki, Bo Sun, Ken Sakata, Motomu Kanai, Shigeki Matsunaga
    • Organizer
      日本化学会 第97春季年会
    • Place of Presentation
      慶應義塾大学日吉キャンパス(神奈川県横浜市)
    • Year and Date
      2017-03-17
    • Related Report
      2016 Annual Research Report
  • [Presentation] Cp*Co(III)触媒を用いたC-H官能基化反応2016

    • Author(s)
      吉野達彦、文野優華、田中亮、池本英也、鈴木雄大、孫博、金井求、松永茂樹
    • Organizer
      第42回反応と合成の進歩シンポジウム
    • Place of Presentation
      清水文化会館マリナート(静岡県静岡市)
    • Year and Date
      2016-11-07
    • Related Report
      2016 Annual Research Report
  • [Presentation] Cp*Co 触媒を用いたピロールのC-Hアルケニル化反応2016

    • Author(s)
      田中亮、池本英也、吉野達彦、金井求、松永茂樹
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      パシフィコ横浜(神奈川県横浜市)
    • Year and Date
      2016-03-29
    • Related Report
      2015 Annual Research Report
  • [Presentation] Cp*Co(III)触媒によるアリルアルコールを用いた芳香族C-Hアリル化反応2016

    • Author(s)
      文野優華、鈴木雄大、吉野達彦、金井求、松永茂樹
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      パシフィコ横浜(神奈川県横浜市)
    • Year and Date
      2016-03-29
    • Related Report
      2015 Annual Research Report

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Published: 2015-08-26   Modified: 2018-03-22  

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