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Creation of Reactive Transition Metal Cyanocarbanions bearing Novel Catalytic Functions as a Substitute of Base

Research Project

Project/Area Number 16350055
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, Graduate School of Engineering Science, Professor, 大学院・基礎工学研究科, 教授 (20164113)

Co-Investigator(Kenkyū-buntansha) IMADA Yasushi  Osaka University, Graduate School of Engineering Science, Associate Professor, 大学院・基礎工学研究科, 助教授 (60183191)
KOMIYA Naruyoshi  Osaka University, Graduate School of Engineering Science, Assistant Professor, 大学院・基礎工学研究科, 助手 (00301276)
TAKAYA Hikaru  Osaka University, Graduate School of Engineering Science, Assistant Professor, 大学院・基礎工学研究科, 助手 (50304035)
Project Period (FY) 2004 – 2005
Project Status Completed (Fiscal Year 2005)
Budget Amount *help
¥14,200,000 (Direct Cost: ¥14,200,000)
Fiscal Year 2005: ¥6,500,000 (Direct Cost: ¥6,500,000)
Fiscal Year 2004: ¥7,700,000 (Direct Cost: ¥7,700,000)
Keywordsruthenium / cyanocarbanion / carbon-carbon bond formation / ルテニウム / シアノカルバニオン錯体
Research Abstract

Transition metal cyanocarbanions are important intermediates for carbon-carbon bond forming reactions. Both C- and N- bound cyanocarbanion complexes were found to be synthesized efficiently, and their interconversion between the two isomers can be controlled by changing a metal center, ligands, and α-substituted group. Spectroscopic and kinetic studies revealed that the isomerization undergoes via a mechanism which is intramolecular slipping of the metal throughout the π-bond of nitrile ligands. Furthermore, reactivities of a series of N- bound ruthenium cyanocarbanion complexes towards aldehydes, ketones, alkynes, and nitriles were investigated by stoichiometiric and catalytic reactions. These studies gave important information about the reaction mechanism of the catalytic Aldol and Michael type reaction, which were previously developed by us.

Report

(3 results)
  • 2005 Annual Research Report   Final Research Report Summary
  • 2004 Annual Research Report
  • Research Products

    (30 results)

All 2006 2005 2004

All Journal Article (19 results) Book (4 results) Patent(Industrial Property Rights) (7 results)

  • [Journal Article] 音で集まる分子2006

    • Author(s)
      直田 健
    • Journal Title

      現代化学 419

      Pages: 24-30

    • NAID

      40007106897

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Annual Research Report 2005 Final Research Report Summary
  • [Journal Article] Rhodium-catalyzed direct aldol condensation of ketones : a facile synthesis of fused aromatic compounds2006

    • Author(s)
      Hiroki Terai et al.
    • Journal Title

      Tetrahedron Lett. 47

      Pages: 1705-1708

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Annual Research Report 2005 Final Research Report Summary
  • [Journal Article] 音で集まる分子の発見2006

    • Author(s)
      直田 健
    • Journal Title

      生産と技術 58

      Pages: 40-43

    • NAID

      40007290653

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Rhodium-Catalyzed Direct Aldol Condensation of Ketones : a Facile Synthesis of Fused Aromatic Compounds2006

    • Author(s)
      Terai Hiroki, Takaya Hikaru, Naota Takeshi
    • Journal Title

      Tetrahedron.Lett. 47

      Pages: 1705-1708

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Molecules That Assemble by Sound2006

    • Author(s)
      Naota Takeshi
    • Journal Title

      Gendaikagaku (in Japanese) 419

      Pages: 24-30

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Discovery of Molecules That Assemble by Sound2006

    • Author(s)
      Naota Takeshi
    • Journal Title

      Seisan to Gijyutsu (in Japanese) 58

      Pages: 40-43

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Molecules That Assemble by Sound : An Application to the Instant Gelation of Stable Organic Fluids2005

    • Author(s)
      Takeshi Naota et al.
    • Journal Title

      J.Am.Chem.Soc. 127

      Pages: 9324-9325

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Annual Research Report 2005 Final Research Report Summary
  • [Journal Article] Flavin-catalyzed generation of diimide : An environmentally friendly method for the aerobic hydrogenation of olefins2005

    • Author(s)
      Yasushi Imada et al.
    • Journal Title

      J.Am.Chem.Soc. 127

      Pages: 14544-14545

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Annual Research Report 2005 Final Research Report Summary
  • [Journal Article] An aerobic, organocatalytic, and chemoselective method for Baeyer-Villiger oxidation2005

    • Author(s)
      Yasushi Imada et al.
    • Journal Title

      Angew.Chem.Int.Ed. 44

      Pages: 1704-1706

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Annual Research Report 2005 Final Research Report Summary
  • [Journal Article] Palladium-Catalyzed Asymmetric Amination and Imidation of 2,3-Allenyl Phosphates2005

    • Author(s)
      Yasushi Imada et al.
    • Journal Title

      Org.Lett. 7

      Pages: 5837-5839

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Annual Research Report 2005 Final Research Report Summary
  • [Journal Article] イリジウム触媒を用いる炭素-炭素結合切断反応の開発とポリマーのケミカルリサイクルへの応用2005

    • Author(s)
      寺井 宏樹 他
    • Journal Title

      環境資源工学 52

      Pages: 92-97

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Molecules That Assemble by Sound : An Application to the Instant Gelation of Stable Organic Fluids2005

    • Author(s)
      Naota Takeshi, Koori Hiroshi
    • Journal Title

      J.Am.Chem.Soc. 127

      Pages: 9324-9325

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Flavin-Catalyzed Generation of Diimede : An Environmentally Friendly Method for the Aerobic Hydrogenation of Olefins2005

    • Author(s)
      Imada Yasushi, Iida Hiroki, Naota Takeshi
    • Journal Title

      J.Am.Chem.Soc. 127

      Pages: 14544-14545

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] An Aerobic, Organocatalytic, and Chemoselective Method for Baeyer-Villiger Oxidation2005

    • Author(s)
      Imada Yasushi, Iida Hiroki, Murahashi Shun-Ichi, Naota Takeshi
    • Journal Title

      Angew.Chem.Int.Ed. 44

      Pages: 1704-1706

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Palladium-Catalyzed Asymmetric Amination and Imidation of 2,3-Allenyl Phosphates2005

    • Author(s)
      Imada Yasushi, Nishida Masayuki, Kutsuwa Koji, Murahashi Shun-ichi, Naota Takeshi
    • Journal Title

      Org.Lett. 7

      Pages: 5837-5839

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Development of Iridium-Catalyzed Carbon-Carbon Bond Cleavage and Application to Polymer-Recycling2005

    • Author(s)
      Terai Hiroki, Takaya Hikaru, Naota Takeshi
    • Journal Title

      Kankyo Shigen Kogaku (in Japanese) 52

      Pages: 92-97

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] An Aerobic, Organocatalytic, and Chemoselective Method for Baeyer-Billiger Oxidation2005

    • Author(s)
      Yasushi Imada et al.
    • Journal Title

      Angew.Chem.Int.Ed. 44

      Pages: 1704-1705

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Oxidation of C-H bonds2004

    • Author(s)
      Naota Takeshi, Komiya Naruyoshi
    • Journal Title

      Catalytic Reactions for Organic Synthesis 103 (Tokyo Kagaku Dojin) (in Japanese)

      Pages: 22-25

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Oxidation by Osmium Tetroxide and Rutenium Tetroxide2004

    • Author(s)
      Naota, Takeshi, Komiya Naruyoshi
    • Journal Title

      Jikken Kagaku Koza, 5th ed. (Maruzen) (in Japanese) vol.17

      Pages: 61-101

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Book] 有機合成のための触媒反応1032004

    • Author(s)
      直田 健 他
    • Publisher
      東京化学同人
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Book] 実験化学講座 第5版17巻2004

    • Author(s)
      直田 健 他
    • Publisher
      丸善
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Book] 有機合成のための触媒反応103(檜山爲次郎, 野崎京子編)2004

    • Author(s)
      直田 健 他
    • Publisher
      東京化学同人
    • Related Report
      2004 Annual Research Report
  • [Book] 第5版 実験科学講座17有機化合物の合成V 酸化反応2004

    • Author(s)
      直田 健 他
    • Publisher
      丸善
    • Related Report
      2004 Annual Research Report
  • [Patent(Industrial Property Rights)] 環状ジニトロン化合物およびその製造方法2006

    • Inventor(s)
      直田 健他
    • Industrial Property Rights Holder
      科学技術振興事業団
    • Filing Date
      2006-03-09
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Patent(Industrial Property Rights)] ゲル化制御剤及びゲル化制御方法2005

    • Inventor(s)
      直田 健他
    • Industrial Property Rights Holder
      科学技術振興事業団
    • Filing Date
      2005-03-16
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Patent(Industrial Property Rights)] 環状ジニトロン化合物およびその製造方法2005

    • Inventor(s)
      直田 健他
    • Industrial Property Rights Holder
      科学技術振興事業団
    • Industrial Property Number
      2005-067786
    • Filing Date
      2005-03-10
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Patent(Industrial Property Rights)] ゲル化制御剤及びゲル化制御方法2005

    • Inventor(s)
      直田 健 他
    • Industrial Property Rights Holder
      科学技術振興事業団
    • Filing Date
      2005-03-25
    • Related Report
      2005 Annual Research Report
  • [Patent(Industrial Property Rights)] 環状ジニトロン化合物およびその製造方法2005

    • Inventor(s)
      直田 健 他
    • Industrial Property Rights Holder
      科学技術振興事業団
    • Filing Date
      2005-03-10
    • Related Report
      2005 Annual Research Report
  • [Patent(Industrial Property Rights)] ゲル化制御剤及びゲル化制御方法2005

    • Inventor(s)
      直田 健, 他
    • Industrial Property Rights Holder
      科学技術振興事業団
    • Filing Date
      2005-03-25
    • Related Report
      2004 Annual Research Report
  • [Patent(Industrial Property Rights)] 環状ジニトロン化合物およびその製造方法2005

    • Inventor(s)
      直田 健, 他
    • Industrial Property Rights Holder
      大阪大学, 科学技術振興事業団
    • Filing Date
      2005-03-10
    • Related Report
      2004 Annual Research Report

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Published: 2004-04-01   Modified: 2016-04-21  

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