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Oxidative cross-coupling of enolate species

Research Project

Project/Area Number 26410046
Research Category

Grant-in-Aid for Scientific Research (C)

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

Principal Investigator

Amaya Toru  大阪大学, 工学研究科, 助教 (20397615)

Project Period (FY) 2014-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000)
Fiscal Year 2016: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000)
Fiscal Year 2015: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2014: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000)
Keywords酸化的クロスカップリング / ボロンエノラート / バナジウム / シリルエノラート / 酸化的カップリング
Outline of Final Research Achievements

Oxidative cross-coupling of enolate species is a useful reaction to synthesize unsymmetrical 1,4-dicarbonyl compounds directly from two different enolate species. However, the formation of homo-coupling product has been an issue in this reaction. In this study, we aimed to develop a method for the selective oxidative cross-coupling of enolate species. The key of our strategy is based on the control of the reactivity by the counter cation metal species of the enolate. As a result, we achieved to demonstrate that the oxidative cross-coupling proceeds selectively by combining boron enolate and silyl enolate in the presence of vanadium (V) as an oxidant.

Report

(5 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Research-status Report
  • 2015 Research-status Report
  • 2014 Research-status Report
  • Research Products

    (18 results)

All 2017 2016 2015 2014

All Journal Article (2 results) (of which Peer Reviewed: 2 results,  Acknowledgement Compliant: 2 results) Presentation (15 results) (of which Int'l Joint Research: 4 results,  Invited: 7 results) Book (1 results)

  • [Journal Article] Vanadium(V)-induced Oxidative Cross-coupling of Various Boron and Silyl Enolates2017

    • Author(s)
      Toru Amaya, Yuma Osafune, Yusuke Maegawa, Toshikazu Hirao
    • Journal Title

      Chemistry -An Asian Journal

      Volume: -

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Selective Intermolecular Oxidative Cross-Coupling of Enolates2015

    • Author(s)
      Toru Amaya, Yusuke Maegawa, Takaya Masuda, Yuma Osafune, Toshikazu Hirao
    • Journal Title

      Journal of The American Chemical Society

      Volume: 137 Issue: 32 Pages: 10072-10075

    • DOI

      10.1021/jacs.5b05058

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] レドックス化学に基づく炭素-炭素結合形成2017

    • Author(s)
      雨夜 徹
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶応義塾大学 日吉キャンパス
    • Year and Date
      2017-03-16
    • Related Report
      2016 Research-status Report
    • Invited
  • [Presentation] Oxovanadium(V)-induced Oxidative Cross-Coupling of Various Boron and Silyl Enolates2017

    • Author(s)
      Toru Amaya
    • Organizer
      International Symposium on Pure & Applied Chemistry (ISPAC 2017)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] エノラート種の酸化的クロスカップリング:エノラート種の検討と触媒化2017

    • Author(s)
      雨夜 徹、長船雄馬、平尾俊一
    • Organizer
      第41回有機電子移動化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] エノラート種の酸化的クロスカップリング2017

    • Author(s)
      雨夜 徹
    • Organizer
      2017日本化学会中国四国支部大会
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 機能有機化学-レドックス反応開発、導電性高分子、スマネン-2017

    • Author(s)
      雨夜 徹
    • Organizer
      第2回有機若手ワークショップ
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 機能有機化学-レドックス型反応開発、導電性ポリアニリン機能システム、ボウル型分子スマネンの化学-2017

    • Author(s)
      雨夜 徹
    • Organizer
      第20回スクリプス・バイオメディカルフォーラム
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] Oxidative Cross-coupling of Boron and Silyl Enolates2016

    • Author(s)
      Toru Amaya, Yusuke Maegawa, Takaya Masuda, Yuma Osafune, Toshikazu Hirao
    • Organizer
      Catalysis and Fine Chemicals 2016 (C&FC 2016)
    • Place of Presentation
      Howard Civil Service International House
    • Year and Date
      2016-11-11
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Oxovanadium(V)-catalyzed Oxidative Cross-Coupling between Different Enolates2016

    • Author(s)
      Yuma Osafune, Toru Amaya, Toshikazu Hirao
    • Organizer
      The 10th International Vanadium Symposium (V10)
    • Place of Presentation
      Howard Civil Service International House
    • Year and Date
      2016-11-07
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] Selective Intermolecular Oxidative Cross-Coupling of Enolates2016

    • Author(s)
      Toru Amaya, Yusuke Maegawa, Takaya Masuda, Yuma Osafune, Toshikazu Hirao
    • Organizer
      The 12th International Symposium on Organic Reactions (ISOR-12)
    • Place of Presentation
      京都テルサ
    • Year and Date
      2016-04-18
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] 高原子価バナジウム触媒によるエノラートの酸化的クロスカップリング2016

    • Author(s)
      雨夜 徹、長船雄馬、平尾俊一
    • 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 Research-status Report
  • [Presentation] 高原子価バナジウムを用いた異種エノラート間の酸化的クロスカップリングおよび触媒化2015

    • Author(s)
      雨夜 徹、長船雄馬、前川祐輔、平尾俊一
    • Organizer
      酸化反応化学討論会
    • Place of Presentation
      同志社大学 今出川キャンパス
    • Year and Date
      2015-10-23
    • Related Report
      2015 Research-status Report
  • [Presentation] オキソバナジウム(V)による異種エノラート間の酸化的クロスカップリング反応および触媒化2015

    • Author(s)
      長船雄馬、前川祐輔、雨夜 徹、平尾俊一
    • Organizer
      第5回CSJ化学フェスタ2015
    • Place of Presentation
      タワーホール船堀
    • Year and Date
      2015-10-13
    • Related Report
      2015 Research-status Report
  • [Presentation] オキソバナジウム(V)を用いるボロン及びシリルエノラートの選択的な酸化的クロスカップリング2015

    • Author(s)
      雨夜 徹、前川祐輔、平尾俊一
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部
    • Year and Date
      2015-03-27
    • Related Report
      2014 Research-status Report
  • [Presentation] オキソバナジウム(V)による異種エノラート間の酸化的クロスカップリング反応の触媒化2015

    • Author(s)
      雨夜 徹、長船雄馬、前川祐輔、平尾俊一
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部
    • Year and Date
      2015-03-27
    • Related Report
      2014 Research-status Report
  • [Presentation] オキソバナジウム(V)を活用するボロン及びシリルエノラートの酸化的クロスカップリング2014

    • Author(s)
      雨夜 徹、前川祐輔、平尾俊一
    • Organizer
      第106回有機合成シンポジウム
    • Place of Presentation
      早稲田大学
    • Year and Date
      2014-11-06 – 2014-11-07
    • Related Report
      2014 Research-status Report
  • [Book] Functionalized Redox Systems2015

    • Author(s)
      Toshikazu Hirao, Toshiyuki Moriuchi, Toru Amaya, Akiya Ogawa, and Akihiro Nomoto
    • Total Pages
      152
    • Publisher
      Springer
    • Related Report
      2014 Research-status Report

URL: 

Published: 2014-04-04   Modified: 2019-03-29  

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