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Development of catalytic cross-pinacol coupling reaction based on the design of highly controlled reaction site

Research Project

Project/Area Number 24655079
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Synthetic chemistry
Research InstitutionOsaka University

Principal Investigator

HIRAO Toshikazu  大阪大学, 工学(系)研究科(研究院), 教授 (90116088)

Co-Investigator(Kenkyū-buntansha) AMAYA Toru  大阪大学, 工学研究科, 助教 (20397615)
Project Period (FY) 2012-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2014: ¥650,000 (Direct Cost: ¥500,000、Indirect Cost: ¥150,000)
Fiscal Year 2013: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2012: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywordsピナコールカップリング / 二核錯体 / 反応場 / バナジウム / チタン / ヘキサアリールベンゼン / 2核錯体 / 2核錯体
Outline of Final Research Achievements

The reductive coupling reactions of carbonyl compounds provide an important method for the construction of a vicinally functionalized carbon-framework. However, the intermolecular cross-pinacol coupling reaction is still a challenging issue due to the difficulty in the discrimination of two aldehydes in the reaction. In this context, we envisioned that the controlled arrangement of two metals on the rigid scaffold can provide spatially regulated reaction sites for the cross-pinacol coupling reaction. As a result, intermolecular cross-pinacol coupling reaction between aliphatic and aromatic aldehydes using hetero dinuclear dihemisalen complexes with vanadium(V) and titanium(IV) on the hexaaryl benzene scaffold was achieved.

Report

(4 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Research-status Report
  • 2012 Research-status Report
  • Research Products

    (9 results)

All 2015 2014 2013 2012

All Journal Article (2 results) (of which Peer Reviewed: 2 results) Presentation (6 results) (of which Invited: 2 results) Book (1 results)

  • [Journal Article] Synthesis of Heterodinuclear Hemisalen Complexes on a Hexaarylbenzene Scaffold and their Application for the Cross-Pinacol Coupling Reaction2014

    • Author(s)
      Akihiro Miyasaka, Toru Amaya, and Toshikazu Hirao
    • Journal Title

      Chemistry A Europian Journal

      Volume: 20 Issue: 6 Pages: 1615-1621

    • DOI

      10.1002/chem.201303946

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Design and synthesis of dinuclear hemisalen complex on hexaarylbenzene scaffold2012

    • Author(s)
      Akihiro Miyasaka
    • Journal Title

      Tetrahedron Letters

      Volume: 53 Issue: 42 Pages: 5589-5592

    • DOI

      10.1016/j.tetlet.2012.07.127

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Presentation] 新しい研究領域を目指して2015

    • Author(s)
      平尾俊一
    • Organizer
      有機合成新春講演会
    • Place of Presentation
      大阪科学技術センター
    • Year and Date
      2015-01-20
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] 機能的レドックス 系の構築に魅せられて2014

    • Author(s)
      平尾俊一
    • Organizer
      大阪大学基礎工学研究科特別講演
    • Place of Presentation
      大阪大学豊中キャンパス
    • Year and Date
      2014-12-12
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Dinuclear Hemisalen Catalyst for Cross-Pinacol Coupling Reaction2013

    • Author(s)
      宮坂彰浩、雨夜 徹、平尾俊一
    • Organizer
      第60回有機金属化学討論会
    • Place of Presentation
      学習院大学目白キャンパス
    • Related Report
      2013 Research-status Report
  • [Presentation] クロスピナコールカップリング反応のための二核ヘミサレン錯体の合成と触媒機能2013

    • Author(s)
      宮坂彰浩
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学びわこ・くさつキャンパス
    • Related Report
      2012 Research-status Report
  • [Presentation] Catalytic Cross-Pinacol Coupling Reaction Using Dinuclear Hemisalen Complex2012

    • Author(s)
      宮坂彰浩
    • Organizer
      XXV International Conference on Organometallic Chemistry (XXV ICOMC)
    • Place of Presentation
      リスボン大学
    • Related Report
      2012 Research-status Report
  • [Presentation] クロスピナコールカップリング反応のための二核金属触媒の開発2012

    • Author(s)
      宮坂彰浩
    • Organizer
      第2回CSJ化学フェスタ2012
    • Place of Presentation
      東京工業大学
    • Related Report
      2012 Research-status Report
  • [Book] Functionalized Redox Systems2015

    • Author(s)
      Toshikazu Hirao
    • Total Pages
      152
    • Publisher
      Springer
    • Related Report
      2014 Annual Research Report

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Published: 2013-05-31   Modified: 2019-07-29  

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