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Development of novel trifluoromethyl radical sources

Research Project

Project/Area Number 16K17869
Research Category

Grant-in-Aid for Young Scientists (B)

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

Principal Investigator

Kawamoto Takuji  山口大学, 大学院創成科学研究科, 助教 (70756139)

Research Collaborator SASAKI Rio  山口大学, 大学院創成科学研究科, 大学院生
ORITANI Kyohei  山口大学, 大学院創成科学研究科, 大学院生
SHIMAYA Yudai  山口大学, 大学院創成科学研究科, 大学院生
MII Junya  山口大学, 大学院創成科学研究科, 大学院生
KAWABATA Atsushi  山口大学, 大学院創成科学研究科, 大学院生
KAMIMURA Akio  山口大学, 大学院創成科学研究科, 教授
Project Period (FY) 2016-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2017: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2016: ¥2,860,000 (Direct Cost: ¥2,200,000、Indirect Cost: ¥660,000)
Keywordsトリフルオロメチル / ラジカル / トリエチルボラン / トリフルオロメタンスルホン酸無水物 / トリフルオロメチル化 / 有機化学
Outline of Final Research Achievements

Trifluoromethylated compounds are the most important class of structural motifs, especially in the fields of pharmaceuticals, agrochemicals, and fine chemicals. α-Trifluoromethylated ketones are useful building blocks that can serve as versatile precursors to drug-like compounds. For the preparation of such α-trifluoromethylated ketones, several methods have been developed. All these methods require external trifluoromethyl sources, which often contain large activating groups. In this work, we have developed a novel method using trifluoromethanesulfonic anhydride as the activator for the ketone and as the trifluoromethyl source.

Report

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

    (21 results)

All 2018 2017 2016 Other

All Int'l Joint Research (1 results) Journal Article (4 results) Presentation (14 results) (of which Int'l Joint Research: 2 results,  Invited: 1 results) Patent(Industrial Property Rights) (2 results)

  • [Int'l Joint Research] University of Pittsburgh(米国)

    • Related Report
      2017 Annual Research Report
  • [Journal Article] Thiol-Catalyzed Radical Decyanation of Aliphatic Nitriles with Sodium Borohydride2018

    • Author(s)
      Kawamoto Takuji、Oritani Kyohei、Curran Dennis P.、Kamimura Akio
    • Journal Title

      Organic Letters

      Volume: 20 Issue: 7 Pages: 2084-2087

    • DOI

      10.1021/acs.orglett.8b00626

    • Related Report
      2017 Annual Research Report
  • [Journal Article] Tris(trimethylsilyl)silane-mediated Reductive Decyanation and Cyano Transfer Reactions of Malononitriles2018

    • Author(s)
      Kawamoto Takuji、Yudai Shimaya、Curran Dennis P.、Kamimura Akio
    • Journal Title

      Chemstry Letters

      Volume: 47 Issue: 4 Pages: 573-575

    • DOI

      10.1246/cl.171231

    • NAID

      130006638884

    • Related Report
      2017 Annual Research Report
  • [Journal Article] Synthesis of α-Trifluoromethylated Ketones from Vinyl Triflates in the Absence of External Trifluoromethyl Sources2017

    • Author(s)
      Kawamoto Takuji、Sasaki Rio、Kamimura Akio
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 56 Issue: 5 Pages: 1342-1345

    • DOI

      10.1002/anie.201608591

    • Related Report
      2017 Annual Research Report 2016 Research-status Report
  • [Journal Article] N-Heterocyclic Carbene Boryl Iodides Catalyze Insertion Reactions of N-Heterocyclic Carbene Boranes and Diazoesters2017

    • Author(s)
      Allen Thomas H.、Kawamoto Takuji、Gardner Sean、Geib Steven J.、Curran Dennis P.
    • Journal Title

      Organic Letters

      Volume: 19 Issue: 13 Pages: 3680-3683

    • DOI

      10.1021/acs.orglett.7b01777

    • Related Report
      2017 Annual Research Report
  • [Presentation] トリフルオロメタンスルホン酸無水物/DABCOを用いるアリールアルキンの二官能基化反応2018

    • Author(s)
      三井準也,川本拓治,上村明男
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] NHC-ボランを用いたアリールスルホンのラジカルホウ素化反応の開発2018

    • Author(s)
      森岡 翼,川本拓治,上村明男,Curran Dennis P
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] エノールトリフラートを用いる新しいトリフルオロメチル化反応2017

    • Author(s)
      川本拓治
    • Organizer
      有機合成化学協会九州山口支部第2回有機合成化学講演会
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 共役ビニルトリフラートを用いるトリフルオロメチル化反応の開発2017

    • Author(s)
      佐々木理緒,川本拓治,上村明男
    • Organizer
      有機合成化学協会九州山口支部第29回若手研究者のためのセミナー
    • Related Report
      2017 Annual Research Report
  • [Presentation] ボロヒドリドを用いた還元的脱シアノ化反応におけるチオールの添加効果2017

    • Author(s)
      折谷亨平,川本拓治,上村明男,Curran Dennis P.
    • Organizer
      日本化学会第97春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] One-pot反応によるα-トリフルオロメチルケトンの合成2017

    • Author(s)
      川本拓治,佐々木理緒,高田凌太郎,上村明男
    • Organizer
      第40回フッ素化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] アルキンの二官能基化反応の開発2017

    • Author(s)
      三井準也,川本拓治,上村明男
    • Organizer
      2017年日本化学会中国四国支部大会 鳥取大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 水素化ホウ素ナトリウムを用いるラジカル脱トシル化反応の開発2017

    • Author(s)
      川端淳嗣,折谷享平,川本拓治,上村明男
    • Organizer
      2017年日本化学会中国四国支部大会 鳥取大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Trifluoromethylation of Enol Triflates2017

    • Author(s)
      川本拓治
    • Organizer
      第2回大津会議 合同研究発表会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 共役エノールトリフラートを用いるトリフルオロメチル化反応の開発2017

    • Author(s)
      川本拓治,佐々木理緒,上村明男
    • Organizer
      第7回フッ素化学若手の会
    • Related Report
      2017 Annual Research Report
  • [Presentation] ビニルトリフラートを用いたαートリフルオロメチルケトンの合成2017

    • Author(s)
      佐々木理緒,川本拓治,上村明男
    • Organizer
      第27回万有福岡シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] One-pot α-Trifluoromethylation of Acetophenones via Vinyl Triflates2016

    • Author(s)
      Sasaki, R.; Kawamoto, T.; Kamimura, A.
    • Organizer
      The 10th International Symposium on Integrated Synthesis
    • Place of Presentation
      淡路夢舞台国際会議場(兵庫県淡路市)
    • Year and Date
      2016-11-18
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] Radical Trifluoromethylation of Vinyl Triflates2016

    • Author(s)
      Sasaki, R.; Kawamoto, T.; Kamimura, A.
    • Organizer
      12th International Symposium on Organic Free Radicals
    • Place of Presentation
      Shanghai, China
    • Year and Date
      2016-10-09
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] ビニルトリフラートをCF3ラジカル源およびラジカルアクセプターとして用いたα―トリフルオロメチルケトンの合成2016

    • Author(s)
      佐々木理緒,川本拓治,上村明男
    • Organizer
      第39回フッ素化学討論会
    • Place of Presentation
      佐賀アバンセ(佐賀県佐賀市)
    • Year and Date
      2016-09-29
    • Related Report
      2016 Research-status Report
  • [Patent(Industrial Property Rights)] ビニルフルオロアルカンスルホナート化合物及びその製法2017

    • Inventor(s)
      川本拓治・佐々木理緒・上村明男
    • Industrial Property Rights Holder
      山口大学
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2017-159859
    • Filing Date
      2017
    • Related Report
      2017 Annual Research Report
  • [Patent(Industrial Property Rights)] ビニルフルオロアルカンスルホナート化合物の製造方法2017

    • Inventor(s)
      川本拓治・三井準也・上村明男
    • Industrial Property Rights Holder
      山口大学
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2017-217052
    • Filing Date
      2017
    • Related Report
      2017 Annual Research Report

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Published: 2016-04-21   Modified: 2022-06-09  

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