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Exploitation of New Synthetic Reactions via C-H Bond Activation by Transition Metal Catalysts

Research Project

Project/Area Number 07455363
Research Category

Grant-in-Aid for Scientific Research (B)

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

Principal Investigator

FUJIWARA Yuzo  Kyushu Univ. Fac. of Eng., Dep't of Chemical Science and Technology, Professor, 工学部, 教授 (10029481)

Co-Investigator(Kenkyū-buntansha) NAGATA Kensuke  Kyushu Univ. Fac. of Eng., Dep't of Chemical Science and Technology, Assistant, 工学部, 助手 (40264080)
TANIGUCHI Yuki  Kyushu Univ. Fac. of Eng., Dep't of Chemical Science and Technology, Assistant, 工学部, 助手 (50217139)
KITAMURA Tsugio  Kyushu Univ. Fac. of Eng., Dep't of Chemical Science and Technology, Associate P, 工学部, 助教授 (00153122)
Project Period (FY) 1995 – 1996
Project Status Completed (Fiscal Year 1996)
Budget Amount *help
¥7,400,000 (Direct Cost: ¥7,400,000)
Fiscal Year 1996: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 1995: ¥6,400,000 (Direct Cost: ¥6,400,000)
KeywordsC-H Bond Activation / Carbon Monoxide / Alkane / Arene / Aminomethylation / Aromatic Acid / Amine Synthesis / Propane / アルカンの活性化 / メチルアミンN-オキシド / エタン / 銅触媒 / アルカンのアミノメチル化 / プロパンのアミノメチル化 / エタンのアミノメチル化 / 酢酸銅 / アルカンへの官能基導入 / アルカンの合成化学的利用
Research Abstract

Our research on this project has discovered and developed the following two new synthetic reactions : 1) carboxylation of arenes with CO by palladium catalysts under very mild conditions, and 2) aminomethylation of alkanes with methyl-tert-amine N-oxides by copper catalysts.
1. Carboxylation of Arenes with CO by Palladium Catalysts under Very Mild Conditions
(1) The Pd (OAc)_2 catalyzed carboxylation reaction of aromatic compounds such as benzene, toluene, anisole, chlorobenzene, and naphthalene with CO in the presence of trifluoroacetic acid and K_2S_2O_8, to give the corresponding aromatic carboxylic acids in high yields under the vary mild conditions (1 atm CO,room temperature) has been discovered.
(2) The reaction proceeds electrophilically with o, p-orientation when an electron-releasing group is attached to the benzene ring.
2. Aminomethylation of Alkanes with Methyl-tert-amine N-oxides by Copper Catalysts
(1) The Cu (OAc)_2/K_2S_2O_8/CF_3 COOH system has been found to cause the aminomethylation reaction of alkanes (10 atm) with methyl-tert-amine N-oxidess at 150゚C to give the corresponding amines in high yields.
(2) Reactions of propane and ethane with trimetjylamine N-oxide gives N,N'-dimethylisobutylamine and N,N'-dimethylpropylamine, respectively. But methane remains unreacted under the present reaction conditions and the work is underway.

Report

(3 results)
  • 1996 Annual Research Report   Final Research Report Summary
  • 1995 Annual Research Report
  • Research Products

    (15 results)

All Other

All Publications (15 results)

  • [Publications] Yuki Taniguchi: "Palladium (II) Catalyzed Carboxylation of Aromatic Compounds with CO under Very Mild Conditions" Chemistry Letters. 5. 345-346 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Yuki Taniguchi: "A Novel Aminomethylation of Gaseous Alkanes with t-Methylamine N-Oxides via C-H Bond Activation by Cu" J.Organomet.Chem.504. 137-141 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Yuzo Fujiwara: "Exploitation of Synthetic Reactions via C-H Bond Activation by Transition Metal Catalysts." Synlett. 591-599 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Yuki Taniguchi: "Copper (II) Catalyzed Reaction of Gaseous Alkanes with Amine N-Oxides" Catalysis Today. (in press).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] 藤原祐三訳: "有機金属化学事典-遷移金属第3章" 朝倉書店, 2700 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Yuki Taniguchi: "Palladium (II) Catalyzed Carboxylation of Aromatic Compounds with CO under Very Mild Conditions" Chem. Lett.345-346 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Yuki Taniguchi: "A Novel Aminomethylation of Gaseous Alkanes with tert-Methylamine N-Oxides via C-H Bond Activation by Copper (II) Salts" J.Organomet. Chem.504. 137-141 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Yuzo Fujiwara: "Exploitation of Synthetic Reactions via C-H Bond Activation by Transition Metal Catalysts. Carboxylation and Aminomethylation of Alkanes or Arenes" Synlett. 591-599 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Yuki Taniguchi: "Copper (II) Catalyzed Reaction of Gaseous Alkanes with Amine N-Oxides" Catalysis Today. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Yuzo Fujiwara: "Exploitation of Synthetic Reactions via C-H Bond Activation by Transition Metal Catalysts" Synlett. 591-599 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Yuki Taniguchi: "Copper(II)Catalyzed Reaction of Gaseous Alkanes with Amine N-Oxides" Catalysis Today in press.

    • Related Report
      1996 Annual Research Report
  • [Publications] 藤原祐三訳: "有機金属化学事典-遷移金属,第3章" 朝倉書店, 2700 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Y. Taniguchi: "Palladium(II) Catalyzed Carboxylation of Aromatic Compounds with CO under Very Mild Conditions" Chemistry Letters. 345-346 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Y. Taniguchi: "A Novel Aminomethylation of Gaseous Alkanes with tert-Methylamine N-oxides via C-H Bond Activation" J. Organometallic Chemistry. 504. 137-141 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Y. Fujiwara: "Exploitation of Synthetic Reactions via C-H Bond Activation by Transition Metal Catalysts." Synlett. (in press).

    • Related Report
      1995 Annual Research Report

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Published: 1995-04-01   Modified: 2016-04-21  

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