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Development of New Transition Metal-Catalyzed Systems under Oxygen

Research Project

Project/Area Number 11450345
Research Category

Grant-in-Aid for Scientific Research (B).

Allocation TypeSingle-year Grants
Section一般
Research Field Synthetic chemistry
Research InstitutionKYOTO UNIVERSITY

Principal Investigator

UEMURA Sakae  Graduate School of Engineering, KYOTO UNIVERSITY Professor, 工学研究科, 教授 (70027069)

Co-Investigator(Kenkyū-buntansha) NISHIBAYASHI Yoshiaki  Graduate School of Engineering, KYOTO UNIVERSITY Research Associate, 工学研究科, 助手 (40282579)
ITOH Osamu  Graduate School of Engineering, KYOTO UNIVERSITY Research Associate, 工学研究科, 助手 (10026023)
OHE Kouichi  Graduate School of Engineering, KYOTO UNIVERSITY Associate Professor, 工学研究科, 助教授 (90213636)
Project Period (FY) 1999 – 2000
Project Status Completed (Fiscal Year 2000)
Budget Amount *help
¥14,800,000 (Direct Cost: ¥14,800,000)
Fiscal Year 2000: ¥5,100,000 (Direct Cost: ¥5,100,000)
Fiscal Year 1999: ¥9,700,000 (Direct Cost: ¥9,700,000)
KeywordsPalladium (II) Acetate / Oxygen / Alcohol Oxidation / Alkene Oxidation / Hydrotalcite / Fluorous Biphase System / tert-Cyclobutanols / Clay Catalyst / パラジウム(II)-ハイドロタルサイト / アリル位アルコール / ピリジン / 酸素酸化 / 触媒反応
Research Abstract

We disclosed a new palladium (II) catalytic system for oxidation of alcohols. The system consisted of a catalytic amount of Pd (OAc)_2, atmospheric pressure of oxygen as an oxidant, and an organic base such as pyridine in toluene. The finding is as follows : 1) a selective oxidation of primary and secondary alcohols to the corresponding aldehydes and ketones, respectively, 2) oxidation of tertiary cyclobutanols to various organic compounds such as β, γ-unsaturated ketones, cyclopentanone derivatives, tetralone derivatives, and cyclopropyl ketones depending on the kind of substituents on the cyclobutane ring. We also developed a new solid catalyst, palladium (II) hydrotalcite, by the reaction of Pd (OAc)_2 with a basic clay hydrotalcite. This solid catalyst is reusable and also has a characteristic feature in oxidation of unsaturated allylic alcohols such as geraniol and nerol to the corresponding aldehydes without any isomerization at the double bond. All these new findings have been reported in scientific journals of Japan, UK and USA.

Report

(3 results)
  • 2000 Annual Research Report   Final Research Report Summary
  • 1999 Annual Research Report
  • Research Products

    (16 results)

All Other

All Publications (16 results)

  • [Publications] Takahiro Nishimura et al.: "Oxidative Transformation of tert-Cyclobutanols by Palladium Catalysts under Oxygen Atmosphere"J.Org.Chem.. 66・4. 1455-1465 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Nobuyuki Kakiuchi et al: "Pa(II)-Hydrotalcite-Catalyzed Selective Oxidation of Alcohols using Molecular Oxygen"Bull.Chem.Soc.Jpn.. 74・1. 165-172 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Takahiro Nishimura et al: "Palladium(II)-Supported Hydrotalcite as a Catalyst for Selective Oxidation of Alcohols using Molecular Oxygen"Chem.Commun.. 1245-1246 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Takahiro Nishimura et al: "Palladium(II)-Catalyzed Oxidation of Alcohols under an Oxygen Atmosphere in a Fluorous Biphase System (FBS)"J.Chem.Soc., Perkin 1. 4301-4305 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Takahiro Nishimura et al: "Palladium(II)-Catalyzed Oxidation of Terminal Alkenes to Methyl Ketones using Molecular Oxygen"J.Chem.Soc., Perkin 1. 1915-1918 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Takahiro Nishimura et al: "Palladium(II)-Catalyzed Oxidation of Alcohols to Aldehydes and Ketones by Molecular Oxygen"J.Org.Chem.. 64・18. 6750-6755 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Takahiro Nishimura et al: "Oxidative Transformation of tert-Cyclobutanols by Palladium Catalysts under Oxygen Atmosphere"J.Org.Chem.. 66, 4. 1455-1465 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Nobuyuki Kakiuchi et al: "Pa (II)-Hydrotalcite-Catalyzed Selective Oxidation of Alcohols using Molecular Oxygen"Bull.Chem.Soc.Jpn.. 74 1. 165-172 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Takahiro Nishimura et al: "Palladium (II)-Supported Hydrotalcite as a Catalyst for Selective Oxidation of Alcohols using Molecular Oxygen"Chem.Commun.. 1245-1246 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Takahiro Nishimura et al: "Palladium (II)-Catalyzed Oxidation of Alcohols under an Oxygen Atmosphere in a Fluorous Biphase System (FBS)"J.Chem.Soc., Perkin. 1. 4301-4305 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Takahiro Nishimura et al: "Palladium (II)-Catalyzed Oxidation of Terminal Alkenes to Methyl Ketones using Molecular Oxygen"J.Chem.Soc., Perkin. 1. 1915-1918 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Takahiro Nishimura et al: "Palladium (II)-Catalyzed Oxidation of Alcohols to Aldehydes and Ketones by Molecular Oxygen"J.Org.Chem.. 64 18. 6750-6755 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Takahiro Nishimura et al: "Palladium(II)-Supported Hydrotalcite as a Catalyst for Selective Oxidation of Alcohols using Molecular Oxygen"Chem.Commun.. -,14. 1245-1246 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Nobuyuki Kakiuchi et al: "Pa(II)-Hydrotalcite-Catalyzed Selective Oxidation of Alcohols using Molecular Oxygen"Bull.Chem.Soc.Jpn.. 74・1. 165-172 (2001)

    • Related Report
      2000 Annual Research Report
  • [Publications] 西村貴洋: "Palladium (II)-Catalyzed Oxidation of Alcohols to Aldehydes and Ketones"J. Org. Chem.. 64. 6750-6755 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] 西村貴洋: "Palladinm(II)-Catalyzed Oxidative Ring Clearage of tert-Cyclobutanols"J. Am. Chem. Soc.. 121. 2645-2646 (1999)

    • Related Report
      1999 Annual Research Report

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Published: 1999-04-01   Modified: 2016-04-21  

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