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Study on the synthesis of organic molecules with monofluoromethyl or difluoromethyl group

Research Project

Project/Area Number 16K05779
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Synthetic chemistry
Research InstitutionSaga University

Principal Investigator

hanamoto takeshi  佐賀大学, 理工学部, 教授 (20228513)

Project Period (FY) 2016-04-01 – 2020-03-31
Project Status Completed (Fiscal Year 2019)
Budget Amount *help
¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2018: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2017: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2016: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywords有機フッ素化学 / 有機合成反応 / モノフルオロメチルアジリジン / モノフルオロメチルオキサゾリジン / モノフルオロメチルイミダゾリン / モノフルオロメチル基 / トリフルオロメチル基 / ビニルスルフィド / ビニルスルホニウム塩 / 選択的臭素化 / ナノ酸化銅触媒 / ジフルオロメチル基 / 有機工業化学
Outline of Final Research Achievements

Organic molecules bearing fluorine atom(s) significantly contribute to the development in various fields including medicines, agrochemicals, materials, and energy. Among them, we paid attention to organic fluorine compounds containing a monofluoromethyl group or a difluoromethyl group. We demonstrate the following two findings; 1) The property and reactivity of the difluoromethyl group are quite similar to those of the trifluoromethyl group. 2) The chemistry of monofluoromethyl group is slightly different from that of trifluoromethyl group in regard of reactivity, electronic effect, and stability.

Academic Significance and Societal Importance of the Research Achievements

未知の分子を設計・合成し、従来から知られている分子にはなかった機能を持たせることができれば、これまでに未解決だった諸問題に対して新たな指針やひいては解答を与えることも可能となる。有機フッ素化合物は自然界にほとんど存在しない珍しい有機分子のため、フッ素を含む置換基を有機分子の特定の位置に自在に導入できる方法の確立は新規な有機フッ素化合物を合成する上で大変重要である。フッ素を含む置換基としてトリフルオロメチル基を持つ分子の合成や反応は広く検討されてきたが、これまで情報量の少なかった類似部分構造のジフルオロメチル基やモノフルオロメチル基に関する新たな知見を加えることができた意義は大きい。

Report

(5 results)
  • 2019 Annual Research Report   Final Research Report ( PDF )
  • 2018 Research-status Report
  • 2017 Research-status Report
  • 2016 Research-status Report
  • Research Products

    (27 results)

All 2019 2018 2017 2016

All Journal Article (6 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 6 results) Presentation (21 results) (of which Int'l Joint Research: 9 results,  Invited: 2 results)

  • [Journal Article] Stereoselective Synthesis of (Z)-2-Bromo-2-CF3-Vinyl Phenyl Sulfide and its Sonogashira Cross-Coupling Reaction2019

    • Author(s)
      Fukuda Yui、Kikumura Takumi、Sakoda Saki、Ikeda Genki、Nakamura Yuki、Dojyo Masakazu、Yamada Yasunori、Hanamoto Takeshi
    • Journal Title

      Synlett

      Volume: 30 Issue: 07 Pages: 837-840

    • DOI

      10.1055/s-0037-1611750

    • Related Report
      2019 Annual Research Report 2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] A γ-Fluoro β-Acetoxypropyl Sulfonium Salt as an Equivalent of a (Fluoromethyl)vinyl Sulfonium Salt: Reagent for the Facile Synthesis of Monofluoromethylated Cyclopropanes or Aziridines2018

    • Author(s)
      Yuuri Fujiwara, Ryuhei Muta, Keiichi Sato, Hiroaki Haramura, Yasunori Yamada, Takeshi Hanamoto
    • Journal Title

      Synlett

      Volume: 29 Issue: 18 Pages: 2372-2376

    • DOI

      10.1055/s-0037-1611000

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] 含フッ素ビニルスルホニウム塩の合成と合成化学的展開2018

    • Author(s)
      花本猛士
    • Journal Title

      有機合成化学協会誌

      Volume: 印刷中

    • NAID

      130007403457

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Three-Component One-Pot Reactions of 2-Trifluoromethyl-N-nosylaziridine, Primary Amines, and Vinylsulfonium Salts for Convenient Access to CF3-Containing Piperazines2017

    • Author(s)
      Hanamoto Takeshi、Hirotaki Kensuke、Irie Akiko、Nakamura Yuki
    • Journal Title

      Synthesis

      Volume: 49 Issue: 11 Pages: 2488-2494

    • DOI

      10.1055/s-0036-1558963

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Regioselective Synthesis of Difluoromethylated Oxazolidines and 2-Imidazolines2016

    • Author(s)
      石川卓也、吉木道哉、田中智也、尾形健有、山田泰教、花本猛士
    • Journal Title

      Synthesis

      Volume: 48 Issue: 09 Pages: 1322-1330

    • DOI

      10.1055/s-0035-1560414

    • Related Report
      2016 Research-status Report
    • Peer Reviewed
  • [Journal Article] Base-Free Synthesis of CF3-Containing β-Triptamine Derivatives from N-Nosyl-2-CF3-Aziridine and Indoles2016

    • Author(s)
      廣瀧謙亮、山口浩平、花本猛士
    • Journal Title

      Synlett

      Volume: 27 Issue: 20 Pages: 2846-2850

    • DOI

      10.1055/s-0036-1588601

    • Related Report
      2016 Research-status Report
    • Peer Reviewed
  • [Presentation] Cross-coupling reaction of (Z)-2-bromo-2-CF3-vinyl sulfur compounds2019

    • Author(s)
      Takumi Kikumura, Yui Fukuda, Saki Sakoda, Genki Ikeda, Yuki Nakamura, Masakazu Dojyo, Yasunori Yamada, Takeshi Hanamoto
    • Organizer
      International Conference on Fluorine Chemistry 2019 Himeji
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Cycloaddition reaction of 2-monofluoromethyl-N-tosylaziridine with aldehydes2019

    • Author(s)
      Keiichi Sato, Takeshi Hanamoto
    • Organizer
      International Conference on Fluorine Chemistry 2019 Himeji
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis and reactions of (Z)-2-Br-2-CF3-vinyl phenyl sulfide2019

    • Author(s)
      Takeshi Hanamoto
    • Organizer
      19th European Symposium on Fluorine Chemistry
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 2-モノフルオロメチル-N-トシルアジリジンとアルデヒドの[3+2]環化付加反応2019

    • Author(s)
      佐藤慧一、花本猛士
    • Organizer
      第42回フッ素化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] Z-2-ブロモ-2-CF3-ビニルベンジルスルフィドのクロスカップリング反応と合成化学的利用2019

    • Author(s)
      池田源己、花本猛士
    • Organizer
      第42回フッ素化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] β-CH2F-ビニルスルホニウム塩等価体の合成と反応2018

    • Author(s)
      藤原夕莉、牟田龍平、花本猛士
    • Organizer
      第55回化学関連支部合同九州大会
    • Related Report
      2018 Research-status Report
  • [Presentation] β-ブロモ-β-CF3-ビニルスルフィドの選択的合成と反応2018

    • Author(s)
      福田優衣、藤原夕莉、池田源己、牟田龍平、中村祐輝、花本猛士
    • Organizer
      第55回化学関連支部合同九州大会
    • Related Report
      2018 Research-status Report
  • [Presentation] β-CH2F-ビニルスルホニウム塩等価体の合成とCFH2含有三員環への展開2018

    • Author(s)
      藤原夕莉、牟田龍平、佐藤慧一、原村浩彰、山田泰教、花本猛士
    • Organizer
      第41回フッ素化学討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] 福田優衣、藤原夕莉、池田源己、菊村拓己、迫田紗紀、中村祐輝、山田泰教、花本猛士2018

    • Author(s)
      β-ブロモ-β-CF3-ビニルスルフィドの合成化学的利用
    • Organizer
      第41回フッ素化学討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] Cross-copling raction of β-bromo-β-CF3-vinyl sulfide2018

    • Author(s)
      福田優衣、花本猛士
    • Organizer
      The 2nd Tri-U Soochow-Saga-Daegu University International Joint Symposium
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] Synthesis and applications of fluorine(s)-containing vinyl sulfonium salts2018

    • Author(s)
      花本猛士
    • Organizer
      The 2nd Tri-U Soochow-Saga-Daegu University International Joint Symposium
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] β-(トリフルオロメチル)ビニル誘導体の簡便合成2017

    • Author(s)
      中村祐輝、花本猛士
    • Organizer
      第27回万有福岡シンポジウム
    • Related Report
      2017 Research-status Report
  • [Presentation] Ring-opening reaction of 2-tirfluoromethyl-N-nosyl-aziridine under neutral conditions2017

    • Author(s)
      花本猛士
    • Organizer
      the 10th Japanes-French Joint Seminar on Fluorine Chemistry
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Presentation] フルオロアセチレン誘導体の合成研究2017

    • Author(s)
      中村祐輝、花本猛士
    • Organizer
      第40回フッ素化学討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] CF3基を含むピペラジンの簡便合成2017

    • Author(s)
      廣瀧謙亮、入江晶子、中村祐輝、花本猛士
    • Organizer
      第40回フッ素化学討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] Study on the preparation of fluoroacetylene derivatives2017

    • Author(s)
      中村祐輝、花本猛士
    • Organizer
      the Tri-U International Joint Symposium 2017 Daegu-Saga-Soochow University
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Presentation] Synthesis and reactions of fluorinated aziridines2017

    • Author(s)
      花本猛士
    • Organizer
      the Tri-U International Joint Symposium 2017 Daegu-Saga-Soochow University
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] 含フッ素不飽和スルホニウム塩の合成と反応2016

    • Author(s)
      道城正和、花本猛士
    • Organizer
      第39回フッ素化学討論会
    • Place of Presentation
      佐賀県佐賀市
    • Year and Date
      2016-09-29
    • Related Report
      2016 Research-status Report
  • [Presentation] トリフルオロエチリデンマロン酸エステルの合成と反応2016

    • Author(s)
      中村祐輝、花本猛士
    • Organizer
      第39回フッ素化学討論会
    • Place of Presentation
      佐賀県佐賀市
    • Year and Date
      2016-09-29
    • Related Report
      2016 Research-status Report
  • [Presentation] 2-CF3-Ns-アジリジンとインドールの熱による開環反応2016

    • Author(s)
      廣瀧謙亮、山口浩平、花本猛士
    • Organizer
      第39回フッ素化学討論会
    • Place of Presentation
      佐賀県佐賀市
    • Year and Date
      2016-09-29
    • Related Report
      2016 Research-status Report
  • [Presentation] Regioselective ring-opening reactions of 2-difluoromethyl-N-Ts-aziridines2016

    • Author(s)
      Takeshi Hanamoto, Takuya Ishikawa, Michiya Yoshiki, Fumihiro kurosato, Tomoya Tanaka, Kentoo Ogata, Yasunori Yamada
    • Organizer
      18th European Symposium on Fluorine Chemistry
    • Place of Presentation
      Kyiv, Ukraine
    • Year and Date
      2016-08-07
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research

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Published: 2016-04-21   Modified: 2021-02-19  

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