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Development of Rh(I)-Catalyzed Hydroacylation Using a N-Heterocyclic Carbene as a Ligand

Research Project

Project/Area Number 20790003
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionHokkaido University

Principal Investigator

OONISHI Yoshihiro  Hokkaido University, 大学院・薬学研究院, 助教 (70399955)

Project Period (FY) 2008 – 2009
Project Status Completed (Fiscal Year 2009)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2009: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2008: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywordsロジウム / NHC / ヒドロアシル化 / アルデヒド / イオン液体 / アルケン / ジエン
Research Abstract

A Rh(I)-NHC catalyzed hydroacylation of 4-alkenals was investigated. As a result, it was found that the hydroacylation of 4-alkenals using a NHC as a ligands proceeded smoothly, giving cyclopentanone derivatives in high yields. And during the course of my investigation, it was also clear that the reaction of allenyl aldehydes, having an alkyne in the tether, with 10 mol% Rh(I)-NHC complexes at 65℃ produced a 5-8 fused bicyclic ketones in high yields. Furthermore, I succeeded in Rh(I)-catalyzed intramolecular hydroacylation of allenyl aldehydes.

Report

(3 results)
  • 2009 Annual Research Report   Final Research Report ( PDF )
  • 2008 Annual Research Report
  • Research Products

    (24 results)

All 2010 2009 2008 Other

All Journal Article (6 results) (of which Peer Reviewed: 6 results) Presentation (17 results) Remarks (1 results)

  • [Journal Article] Rh(I)-Catalyzed Cycloisomerization of 1, 3-Diene with Alkene in a Tether.2009

    • Author(s)
      Yoshihiro Oonishi, Akira Saito, Miwako Mori, Yoshihiro Sato
    • Journal Title

      Synthesis

      Pages: 969-979

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Study on Rh(I)-catalyzed cycloisomerization of dienes with alkenes in ionic liquids: effect of the structure of ILs on catalyst recyclability.2009

    • Author(s)
      Yoshihiro Oonishi, Akira Saito, Yoshihiro Sato
    • Journal Title

      Green Chem. 11

      Pages: 330-333

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Study on Rh(I)-catalyzed cycloisomerization of dienes with alkenes in ionicliquids : effect of the structure of ILs on catalyst recyclability2009

    • Author(s)
      大西英博
    • Journal Title

      Green Chemistry 11

      Pages: 330-333

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Rh(I)-Catalyzed Cycloisomerization of 1,3-Diene with Alkene in a Tether2009

    • Author(s)
      大西英博
    • Journal Title

      Synthesis

      Pages: 969-979

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Construction of Chiral Quaternary Carbon Centers via Palladium-Catalyzed Asymmetric Deconjugative Allylation.2008

    • Author(s)
      Hiroki Yamamoto, Yoshihiro Oonishi, Yoshihiro Sato
    • Journal Title

      Heterocycles 76

      Pages: 1485-1495

    • NAID

      40016323244

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Construction of Chiral Quaternary Carbon Centers via Palladium-Catalyzed Asymmetric Deconjugative Allylation2008

    • Author(s)
      佐藤美洋
    • Journal Title

      Heterocycles 76

      Pages: 1485-1495

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Presentation] ロジウム触媒を用いたアレン-インとアルデヒドの新規環化反応の開発2010

    • Author(s)
      細谷昭仁, 大西英博, 佐藤美洋
    • Organizer
      日本薬学会第130年
    • Place of Presentation
      岡山大学(岡山)
    • Year and Date
      2010-03-29
    • Related Report
      2009 Final Research Report
  • [Presentation] ロジウム触媒を用いたアレン-インとアルデヒドの新規環化反応の開発2010

    • Author(s)
      細谷昭仁
    • Organizer
      日本薬学会第130年会
    • Place of Presentation
      岡山、岡山大学
    • Year and Date
      2010-03-29
    • Related Report
      2009 Annual Research Report
  • [Presentation] ロジウム触媒によるアレン-インとアルデヒドの分子内環化反応を利用した二環式化合物の合成2010

    • Author(s)
      大西英博, 細谷昭仁, 佐藤美洋
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      近畿大学(大阪)
    • Year and Date
      2010-03-28
    • Related Report
      2009 Final Research Report
  • [Presentation] ロジウム触媒によるアレン・インとアルデヒドの分子内環化反応を利用した二環式化合物の合成2010

    • Author(s)
      大西英博
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      大阪、近畿大学
    • Year and Date
      2010-03-28
    • Related Report
      2009 Annual Research Report
  • [Presentation] Synthesis of Rh(IMes)(dppe)Cl and Its Utilization in Hydroacylation and Cycloisomerization2009

    • Author(s)
      大西英博, 佐々木隆行, 齊藤誠, 佐藤美洋
    • Organizer
      第56回有機金属化学討論会
    • Place of Presentation
      同志社大学(京都)
    • Year and Date
      2009-09-10
    • Related Report
      2009 Final Research Report
  • [Presentation] Rh(I)-Catalyzed Cyclization of Allene-Yne and Tethered Aldehyde2009

    • Author(s)
      細谷昭仁, 大西英博, 佐藤美洋
    • Organizer
      第56回有機金属化学討論会
    • Place of Presentation
      同志社大学(京都)
    • Year and Date
      2009-09-10
    • Related Report
      2009 Final Research Report
  • [Presentation] Rh(I)-Catalyzed Cyclization of Allene-Yne and Tethered Aldehyde2009

    • Author(s)
      細谷昭仁
    • Organizer
      第56回有機金属化学討論会
    • Place of Presentation
      京都、同志社大学
    • Year and Date
      2009-09-10
    • Related Report
      2009 Annual Research Report
  • [Presentation] Synthesis of Rh(IMes)(dppe)Cl and Its Utilization in Hydroacylation and Cycloisomerization2009

    • Author(s)
      大西英博
    • Organizer
      第56回有機金属化学討論会
    • Place of Presentation
      京都、同志社大学
    • Year and Date
      2009-09-10
    • Related Report
      2009 Annual Research Report
  • [Presentation] 二座ホスフィン配位子をもつ新規Rh-NHC錯体の合成とヒドロアシル化反応・環化異性化反応への利用2009

    • Author(s)
      佐々木隆行, 大西英博, 佐藤美洋
    • Organizer
      日本薬学会第129年会
    • Place of Presentation
      国立京都国際会館(京都)
    • Year and Date
      2009-03-27
    • Related Report
      2009 Final Research Report
  • [Presentation] 二座ホスフィン配位子をもつ新規Rh-NHC錯体の合成とヒドロアシル化反応-環化異性化反応への利用2009

    • Author(s)
      佐々木隆行
    • Organizer
      日本薬学会第129年会
    • Place of Presentation
      京都
    • Year and Date
      2009-03-27
    • Related Report
      2008 Annual Research Report
  • [Presentation] Rh(IMes)(dppe)Cl錯体の合成とヒドロアシル化・環化異性化反応への適用2008

    • Author(s)
      佐々木隆行
    • Organizer
      日本薬学会北海道支部第131回例会
    • Place of Presentation
      小樽
    • Year and Date
      2008-11-29
    • Related Report
      2008 Annual Research Report
  • [Presentation] Cationic Rh(I)-Catalyzed Cyclizations in Ils2008

    • Author(s)
      佐藤美洋, 大西英博, 齊藤誠
    • Organizer
      23rd International Conference on Organometallic Chemistry (ICOMC2008)
    • Place of Presentation
      Rennes (France)
    • Year and Date
      2008-07-14
    • Related Report
      2009 Final Research Report 2008 Annual Research Report
  • [Presentation] Nickel(0)-Catalyzed Asymmetric Three-Component Coupling of 1,3-Dienes, Aldehydes, and Silanes Using Chiral N-Heterocyclic Carbenes as Ligands2008

    • Author(s)
      日向優
    • Organizer
      23rd International Conference on Organometallic Chemistry (ICOMC2008)
    • Place of Presentation
      Rennes (France)
    • Year and Date
      2008-07-14
    • Related Report
      2008 Annual Research Report
  • [Presentation] Rh(I)-Catalyzed Cycloisomerization of 1, 3-Diene and Tethered Alkene in Ionic Liquids2008

    • Author(s)
      齊藤誠, 大西英博, 佐藤美洋
    • Organizer
      17th International Conference on Organic Synthesis
    • Place of Presentation
      Daejeon (Korea)
    • Year and Date
      2008-06-26
    • Related Report
      2009 Final Research Report
  • [Presentation] Enyne Metathesis in Ionic Liquids Using an Imidazolium-Tagged Ruthenium Catalysts2008

    • Author(s)
      大西英博, 五十嵐絵里, 川井諒 平, 齋藤望, 佐藤美洋
    • Organizer
      17th International Conference on Organic Synthesis
    • Place of Presentation
      Daejeon (Korea)
    • Year and Date
      2008-06-26
    • Related Report
      2009 Final Research Report
  • [Presentation] Enyne Metathesis in Ionic Liquids U6ing an Imidazohum, Tagged Ruthenium Catalyst2008

    • Author(s)
      大西英博
    • Organizer
      17th International Conference on Organic Synthesis
    • Place of Presentation
      Daejeon (Korea)
    • Year and Date
      2008-06-26
    • Related Report
      2008 Annual Research Report
  • [Presentation] Rh(I)-Catalyzed Cycloisomerization of 1,3-Diene and Tethered Alkene in Ionic Liquids2008

    • Author(s)
      齊藤誠
    • Organizer
      17th International Conference on Organic Synthesis
    • Place of Presentation
      Daejeon (Korea)
    • Year and Date
      2008-06-26
    • Related Report
      2008 Annual Research Report
  • [Remarks]

    • URL

      http://gouka.pharm.hokudai.ac.jp/index.html

    • Related Report
      2009 Final Research Report

URL: 

Published: 2008-04-01   Modified: 2016-04-21  

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