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Catalytic Fluorination of Carbonyl Compounds

Research Project

Project/Area Number 25410048
Research Category

Grant-in-Aid for Scientific Research (C)

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

Principal Investigator

KITAMURA Tsugio  佐賀大学, 工学(系)研究科(研究院), 教授 (00153122)

Project Period (FY) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000)
Fiscal Year 2015: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2014: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2013: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Keywords有機化学 / フッ素化反応 / 超原子価ヨウ素 / 触媒反応 / フルオロカルボニル化合物
Outline of Final Research Achievements

The conventional synthetic method needs dangerous fluorine gas as a fluorine source. Therefore, a safe and convenient fluorination process is desirable.
On the basis of the previous results on hypervalent iodine chemistry, this study is aimed at developing a safe and convenient fluorination reaction without dangerous fluorine gas.
(1) A safe and convenient synthetic method of fluorinated dicarbonyl compounds has been developed by a simple procedure using commercially available hydrofluoric acid and iodosylbenzene. (2) Fluorination of ketones has been developed using HF reagents/PhIO. This method is useful as a convenient fluorination reaction because there are no reports for direct fluorination of ketones. (3) Catalytic fluorination of carbonyl compounds has been developed using iodobenzene catalyst. Since this catalytic fluorination does not need transition metal catalysts, metal-free, epoch-making catalytic fluorination is achieved.

Report

(4 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Research-status Report
  • 2013 Research-status Report
  • Research Products

    (18 results)

All 2016 2015 2014 2013

All Journal Article (5 results) (of which Int'l Joint Research: 2 results,  Peer Reviewed: 5 results,  Acknowledgement Compliant: 3 results) Presentation (13 results) (of which Invited: 1 results)

  • [Journal Article] Hypervalent Iodine-Mediated Fluorination of Styrene Derivatives: Stoichiometric and Catalytic Transformation to 2,2-Difluoroethylarenes2015

    • Author(s)
      Tsugio Kitamura, Kensuke Muta, and Juzo Oyamada
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 80 Issue: 21 Pages: 10431-10436

    • DOI

      10.1021/acs.joc.5b01929

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] A Convenient Synthesis of 2-Fluoro- and 2-Chloromalonic Esters Mediated by Hypervalent Iodine2015

    • Author(s)
      Tsugio Kitamura, Kensuke Muta, Juzo Oyamada
    • Journal Title

      Synthesis

      Volume: 47 Issue: 20 Pages: 3241-3245

    • DOI

      10.1055/s-0034-1378747

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Hypervalent Iodine-Promoted alpha-Fluorination of Acetophenone Derivatives with a TriethylamineHF Complex2014

    • Author(s)
      Tsugio Kitamura, Kensuke Muta, Kazutaka Muta
    • Journal Title

      Journal of Organic Chemistry

      Volume: 79 Issue: 12 Pages: 5842-5846

    • DOI

      10.1021/jo500691b

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Facile Synthesis of 2-Fluoroo-1,3-dicarbonyl Compounds with Aqueous Hydrofluoric Acid Mediated by Iodosylarenes2013

    • Author(s)
      Tsugio Kitamura, Satoshi Kuriki, Kensuke Muta, Mohammad Hasan Morshed, Kazutaka Muta, Keisuke Gondo, Yuji Hori, Masaya Miyazaki
    • Journal Title

      Synthesis

      Volume: 45 Issue: 22 Pages: 3125-3130

    • DOI

      10.1055/s-0033-1339672

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Catalytic fluorination of 1,3-dicarbonyl compounds using iodoarene catalysts2013

    • Author(s)
      Tsugio Kitamura, Kazutaka Muta, Satoshi Kuriki
    • Journal Title

      Tetrahedron Letters

      Volume: 54 Issue: 45 Pages: 6118-6120

    • DOI

      10.1016/j.tetlet.2013.08.129

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] Hypervalent Iodine-Mediated Fluorination of Styrene Derivatives2016

    • Author(s)
      Tsugio Kitamura, Kensuke Muta, Juzo Oyamada
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学京田辺キャンパス
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] 超原子価ヨウ素により促進されるスチレン類のgem-ジフッ素化反応2015

    • Author(s)
      牟田健祐、小山田重蔵、北村二雄
    • Organizer
      第18回ヨウ素学会シンポジウム
    • Place of Presentation
      千葉大学
    • Year and Date
      2015-09-16
    • Related Report
      2015 Annual Research Report
  • [Presentation] 超原子価ヨウ素によって促進されるスチレン類のgem-ジフッ素化反応2015

    • Author(s)
      牟田健祐、北村二雄、小山田重蔵
    • Organizer
      第52回化学関連支部合同九州大会
    • Place of Presentation
      北九州国際会議場
    • Year and Date
      2015-06-27
    • Related Report
      2015 Annual Research Report
  • [Presentation] ヨードシルアレーンにより促進されるカルボニル化合物のフッ素化反応の開発2015

    • Author(s)
      牟田健祐、北村二雄
    • Organizer
      第25回万有福岡シンポジウム
    • Place of Presentation
      九州大学100周年記念講堂
    • Year and Date
      2015-05-16
    • Related Report
      2015 Annual Research Report
  • [Presentation] メタルフリーでヨードシルアレーンにより促進されるカルボニル化合物のフッ素化反応2015

    • Author(s)
      牟田健祐、北村二雄、小山田重蔵
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学船橋キャンパス
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] ヨードシルアレーンを用いたアセトフェノン誘導体の簡便なフッ素化反応2014

    • Author(s)
      牟田健祐、北村二雄
    • Organizer
      第17回 ヨウ素学会シンポジウム
    • Place of Presentation
      千葉大学
    • Year and Date
      2014-09-19
    • Related Report
      2014 Research-status Report
  • [Presentation] Catalytic Fluorination of 1,3-Dicarbonyl Compounds Using an Iodoarene Catalyst 4th International Conference on Hypervalent Iodine Chemistry2014

    • Author(s)
      Kazutaka Muta, Tsugio Kitamura
    • Organizer
      4th International Conference on Hypervalent Iodine Chemistry
    • Place of Presentation
      千葉、成田市
    • Year and Date
      2014-07-02 – 2014-07-05
    • Related Report
      2014 Research-status Report
  • [Presentation] [2,4,5-Tris(trimethylsilyl)phenyl](phenyl)iodonium Triflate: Convenient and Efficient Approach to Various Aryne Precursors2014

    • Author(s)
      sugio Kitamura
    • Organizer
      4th International Conference on Hypervalent Iodine Chemistry
    • Place of Presentation
      千葉、成田市
    • Year and Date
      2014-07-02 – 2014-07-05
    • Related Report
      2014 Research-status Report
    • Invited
  • [Presentation] ヨードシルアレーンを用いたアセトフェノン誘導体の簡便なフッ素化反応2014

    • Author(s)
      牟田健祐、北村二雄
    • Organizer
      第51回化学関連支部合同九州大会
    • Place of Presentation
      北九州市
    • Year and Date
      2014-06-28
    • Related Report
      2014 Research-status Report
  • [Presentation] ヨードアレーンを触媒とする1,3-ジカルボニル化合物のフッ素化反応2014

    • Author(s)
      牟田和高、北村二雄
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Research-status Report
  • [Presentation] ヨードシルアレーンを用いたアセトフェノン誘導体の簡便なフッ素化反応2014

    • Author(s)
      牟田健祐、北村二雄
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Research-status Report
  • [Presentation] ヨードアレーンを触媒とする1,3-ジカルボニル化合物のフッ素化反応2013

    • Author(s)
      北村二雄、牟田和高、栗木聡史
    • Organizer
      第16回 ヨウ素学会シンポジウム
    • Place of Presentation
      千葉大学
    • Related Report
      2013 Research-status Report
  • [Presentation] ヨードアレーンを触媒とする1,3-ジカルボニル化合物のフッ素化反応2013

    • Author(s)
      北村二雄、牟田和高、牟田健祐
    • Organizer
      第40回 有機典型元素化学討論会
    • Place of Presentation
      近畿大学
    • Related Report
      2013 Research-status Report

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Published: 2014-07-25   Modified: 2019-07-29  

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