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Systemization of Palladium Complex Catalysts and Their Application to Organic Synthesis

Research Project

Project/Area Number 09650962
Research Category

Grant-in-Aid for Scientific Research (C)

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

Principal Investigator

KIJI Jitsuo  Tottori University, Faculty of Engineering, Professor, 工学部, 教授 (60026002)

Co-Investigator(Kenkyū-buntansha) TSUJI Jiro  Tokyo Institute of Technology, Emeritus, 名誉教授 (00016685)
OKANO Tamon  Tottori University, Faculty of Engineering, Associate Professor, 工学部, 助教授 (20112104)
Project Period (FY) 1997 – 1999
Project Status Completed (Fiscal Year 1999)
Budget Amount *help
¥3,400,000 (Direct Cost: ¥3,400,000)
Fiscal Year 1999: ¥500,000 (Direct Cost: ¥500,000)
Fiscal Year 1998: ¥1,100,000 (Direct Cost: ¥1,100,000)
Fiscal Year 1997: ¥1,800,000 (Direct Cost: ¥1,800,000)
KeywordsPalladium catalyst / Carbonylation / Olefin-CO copolymerization / Bis-π-allylpalladium / クロスカップリング / Hedk反応 / ブタジエンの環化付加
Research Abstract

The purpose of the present study was to develop palladium-catalyzed synthetic reactions and to elucidate their reaction mechanisms.
1 Derivatives of 2-butyne-1, 4-diol were carbonylated in ethanol in the presence of Pd-phosphine catalyst. Its carbonate of ethyl chloroformate gave bis(methylene)butanedioate in a high yield.
2 Thienyl-substituted 2-butyne-1, 4-diols were carbonylated in benzene in the presence of palladium acetate and iodine to give photochromic bisthienylfulgides in one-pot.
3 Palladium- and copper-catalyzed copolymerizations of carbon monoxide with ethylene or styrene were investigated. Pyrolysis-GC revealed that the polymers obtained were of alternating structures.
4 Allylation of pronucleophiles, and telomerization and cocyclization of buta-diene were investigated under neutral conditions. Their reaction mechanisms were discussed from a viewpoint of amphiphilic nature of the bis-π-allylpalladium intermediate.
5 Styrenes, stilbenes, and poly(phenylene vinylene)s were synthesized by the Heck reaction of ethylene with haloarenes.

Report

(4 results)
  • 1999 Annual Research Report   Final Research Report Summary
  • 1998 Annual Research Report
  • 1997 Annual Research Report
  • Research Products

    (27 results)

All Other

All Publications (27 results)

  • [Publications] Jitsuo Kiji: "A Simple Synthetic Method to Bis (methylene) Butanedioate"Synthesis. 869-870 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] F. Bertini: "Thermal Degradation of Alternating Styrene-Carbon Monoxide Copolymers"J. Anal. Appl. Pyrolysis. 49. 31-42 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Jitsuo Kiji: "Palladium-Catalyzed Arylation of Ethylene"J. Mol. Catal.. 147. 3-10 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] 辻 二郎: "π-アリルパラジウムの化学の誕生と発展"有機合成化学協会誌. 57、12. 1036-1050 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Jitsuo Kiji: "A Convenient and General Synthetic Method for Photochromic Fulgides by Palladium-Catalyzed Carbonylation of 2-Butyne-1,4-diols"Mol. Cryst. Liq. Cryst.. (印刷中). (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Yasushi Yokoyama: "Highly Diastereoselective Photochromic Cyclization of a Bismethylenethienylfulgide"Chem. Lett.. (印刷中). (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] 辻 二郎: "遷移金属が拓く有機合成"化学同人. 270 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Jiro Tsuji: "Transition Metals for Organic Synthesis, Vol. 1 (分担執筆)"Wiley-VCH. 595 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] 木地 実夫: "有機工業化学 そのエッセンス(分担執筆)"裳華房. 313 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] J.Kiji: "A Simple Synthetic Method to Bis(methylene)butandioate"Synthesis. 869-870 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] F.Bertini: "Thermal Degradation of Alternating Styrene-Carbon Monoxide Copolymers"J. Anal. Appl. Pyrolysis. 49. 31-42 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] J.Kiji: "Palladium-Catalyzed Arylation of Ethylene"J. Mol. Catal.. 147. 3-10 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] J.Tsuji: "The Birth and Development of π-Allylpalladium Chemistry"J. Synthetic Org. Chem. Jpn.. 57. 1036-1060 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] J.Kiji: "A Convenient and General Synthetic Method for Photochromic Fulgides by Palladium-Catalyzed Carbonylation of 2-Bytyne-1, 4-diols"Mol. Cryst. Liq. Cryst.. (in press.).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Y.Yokoyama: "Highly Diastereo-selective Photochromic Cyclization of a Bismethylenethienylfulgide"Chem. Lett.. (in press.).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] F.Bertini: "Thermal Degradation of Alternating Styrene-Carbon Monoxide"J.Anal.Appl.Pyrolysis. 49. 31-42 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Jitsuo Kiji: "Palladium-Catalyzed Arylation of Ethylene"J.Mol.Catal.. 147. 3-10 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] 辻 二郎: "π-アリルパラジウムの化学の誕生と発展"有機合成化学協会誌. 57、12. 1036-1050 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Jitsuo Kiji: "A Convenient and General Synthetic Method for Photochromic Fulgides by Palladium-Catalvzed Carbonvlation of 2-Butyne-1,4-diols"Mol.Cryst.Liq.Cryst.. (印刷中). (2000)

    • Related Report
      1999 Annual Research Report
  • [Publications] Yasushi Yokoyama: "Highly Diastereoselective Photochromic Cyclization of a Bismethylenethienylfulgide"Chem.Lett.. (印刷中). (2000)

    • Related Report
      1999 Annual Research Report
  • [Publications] 木地実夫: "有機工業化学 そのエッセンス(分担執筆)"裳華房. 313 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] J.Kiji, T.Okano, H.Kimura, K.Saiki: "Palladium-catalyzed Carbonylative Coupling of Iodobenzene and 2-Methyl-3-butyn-2-ol under Biphasic Conditions" J.Mol.Catal.A : Chem.130. 95-100 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] J.Kiji, T.Okano, A.Ooue.: "Palladium-catalyzed Arylation of Ethylene. A Synthetic Route to Styrene,Stilbene,and Poly (phenlene vinylene) s" J.Mol.Catal.A : Chem.(in press).

    • Related Report
      1998 Annual Research Report
  • [Publications] J.Tsuji, J.Kiji: "M.Beller,C.Bolm Ed. "Transition Metals for Organic Synthesis",Vol.1" Wiley-VCH, 595 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] J.Kiji: "A Simple Synthetic Method to Bis(methylene)butanedioate" Synthesis. No.8. 869-870 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] J.Kiji: "Alternating Olefin-Carbon Monoxide Copolymers and Their Derivatives" J.Anal.Appl.Pyrolysis. 40-41. 331-345 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] 辻 二郎: "遷移金属が拓く有機合成" 化学同人, 270 (1997)

    • Related Report
      1997 Annual Research Report

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Published: 1997-04-01   Modified: 2016-04-21  

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