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Synthesis and Reactivity of C-and N-Bound Transitionmetal α-Cyanocarbanions

Research Project

Project/Area Number 13450371
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Synthetic chemistry
Research InstitutionOsaka University

Principal Investigator

NAOTA Takeshi  Osaka University, Department of Chemistry Graduate School of Engineering Science, Professor, 大学院・基礎工学研究科, 教授 (20164113)

Project Period (FY) 2001 – 2003
Project Status Completed (Fiscal Year 2003)
Budget Amount *help
¥7,100,000 (Direct Cost: ¥7,100,000)
Fiscal Year 2003: ¥1,800,000 (Direct Cost: ¥1,800,000)
Fiscal Year 2002: ¥2,300,000 (Direct Cost: ¥2,300,000)
Fiscal Year 2001: ¥3,000,000 (Direct Cost: ¥3,000,000)
Keywordscyanocarbanion / ruthenium / Michael reaction / Aldol reaction / α-シアノカルバニオン
Research Abstract

A novel N-bound Cp ruthenium carbanion complex was synthesized to apply for the C-C bond formation reactions such as Aldol and Michael reactions. The complex can be reacted with various olefins bearing electron-withdrawing substituents to give the corresponding N-bound ruthenium complex, of which ligand was converted to Michael type adducts. Furthermore, N-bound hydrido ruthenium carbanion complex with α-alkoxycarbonyl group, as well as the complex mentioned above, was found to react with an electron deficient olefin without loss of metal-hydrido. The result suggests that catalytic Michael addition of metal-hydrido, which is generated by C-H activation of substrates, proceeds with ionic mechanism rather than hydrometalation.

Report

(4 results)
  • 2003 Annual Research Report   Final Research Report Summary
  • 2002 Annual Research Report
  • 2001 Annual Research Report
  • Research Products

    (16 results)

All Other

All Publications (16 results)

  • [Publications] Naota Takeshi, Tannna Akio, Murahashi Shun-Ichi: "Carbon-Carbon Bond Forming Reactions of N-Bound Transition Metal α-Cyanocarbanions : a Mechanistic Probe for Catalytic Michael Reactions of Nitriles"Chem.Commun.. 63-64 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Murahashi Shun-Ichi, Takaya Hikaru, Naota Takeshi: "Ruthenium Catalysis in Organic Synthesis"Pure Appl.Chem.. 74. 19-24 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Naota Takeshi, Tannna Akio, Kamuro Shigeaki, Murahashi Shun-Ichi: "Mechanism of the Interconversions between C- and N-Bound Transition Metal α-Cyanocarbanions"J.Am.Chem.Soc.. 124. 6842-6843 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] 直田 健, 小宮成義: "有機合成のための触媒反応103"東京化学同人. 22-25 (2004)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] 直田 健, 小宮成義: "実験化学講座 第5版17巻"丸善(印刷中). (2004)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Naota Takeshi, Tannna Akio, Murahashi Shun-Ichi: "Carbon-Carbon Bond Forming Reactions of N-Bound Transition Metal α-Cyanocarbanions : a Mechanistic Probe for Catalytic Michael Reactions of Nitriles"Chem.Commun.. 63-64 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Murahashi Shun-Ichi, Takaya Hikaru, Naota Takeshi: "Ruthenium Catalysis in Organic Synthesis"Pure Appl.Chem.. 74. 19-24 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Naota Takeshi, Tannna Akio, Kamuro Shigeaki, Murahashi Shun-Ichi: "Mechanism of the Interconversions between C-and N-Bound Transition Metal α-Cyanocarbanions"J.Am Chem.Soc.. 124. 6842-6843 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Naota, Takeshi, Komiya Naruyoshi: "Catalytic Reactions for Organic Synthesis 103 (in Japanese)"Tokyo Kagaku Dojin. 22-25 (2004)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Naota Takeshi, Komiya Naruyoshi: "Jikken Kagaku Koza, 5th ed, vol 17 (in Japanese)"Maruzen (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] 直田 健, 小宮成義他: "有機合成における触媒反応"東京化学同人(in press). (2004)

    • Related Report
      2003 Annual Research Report
  • [Publications] 直田 健, 小宮成義他: "実験化学講座 第5版 17巻"丸善(in press). (2004)

    • Related Report
      2003 Annual Research Report
  • [Publications] Takeshi Naota, Akio Tannna, Shigeaki Kamuro, ShuuIchi Murahashi: "Mechanism of the Interconversions between C-and N-Bound Transition Metal α-Cyanocarbanions"J. Am. Chem. Soc.. 124. 6842-6843 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] 直田健, 小宮成義ほか: "有機合成における触媒反応"東京化学同人(in press). (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] Takeshi Naota, Akio Tannna, Shun-Ichi Murahashi: "Carbon-Carbon Bond Forming Reactions of N-Bound Transition Metal α-Cyanocarbanions"Chem. Commun.. 63-64 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Shun-Ichi Murahashi, Naruyoshi Komitam, Yoshiaki Oda, Toshiyuki Kuwabara, Takeshi Naota: "Ruthenium-Catalyzed Oxidation of Alkenes with Tert-Butyl Hydoroperoxide and Pracetic Acid"J. Org. Chem.. 65. 9186-9193 (2001)

    • Related Report
      2001 Annual Research Report

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Published: 2001-04-01   Modified: 2016-04-21  

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