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Development of dehydrogenation reaction using palladium catalyst and ethylene system

Research Project

Project/Area Number 13554022
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section展開研究
Research Field Organic chemistry
Research InstitutionKobe University

Principal Investigator

HAYASHI Masahiko  Kobe University, Faculty of Science, Professor, 理学部, 教授 (60192704)

Co-Investigator(Kenkyū-buntansha) MATSUSHITA Akio  Ube Industry, Team leader (Researcher), 有機合成第2研究部, 主席研究員
HARADA Katsumasa  Ube Industry, Director (Researcher), 有機合成第2研究部, 部長(研究職)
YAMAZAKI Suzuko  Yamaguchi University, Faculty of Science, Associate Professor, 理学部, 助教授 (80202240)
SHIN Jyun-ichi  Ube Industry, Researcher, 有機合成第2研究部, 研究員
Project Period (FY) 2001 – 2003
Project Status Completed (Fiscal Year 2003)
Budget Amount *help
¥8,700,000 (Direct Cost: ¥8,700,000)
Fiscal Year 2003: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 2002: ¥1,100,000 (Direct Cost: ¥1,100,000)
Fiscal Year 2001: ¥6,600,000 (Direct Cost: ¥6,600,000)
Keywordspalladium catalyst / oxidative aromatization / heterocyclic compound / activated carbon / envirornmentally friendly reaction / ヘテロ環 / パラジウム / 脱水素反応 / 酸化反応 / ピペリジン / ピラゾール / 複素環化合物 / 芳香族化 / 環境調和型反応
Research Abstract

Recently reported oxidation process of alcohols using molecular oxygen as an oxidizing agent in the presence of catalytic amount of transition metals such as copper, ruthenium, and palladium compounds will be reviewed. Oxidation of alcohols based on hydrogen transfer reaction between alcohols and simple olefins such as ethylene is also described. That is, some benzylic and allylic alcohols can be converted into the corresponding carbonyl compounds using a catalytic amount of palladium on activated carbon (Pd-C) under ethylene atmosphere. The combination of Pd(OAc)2 and vinyl acetate also works efficiently. Selective oxidation of hydroxy groups on carbohydrates (D-glycals) and steroids as well as simpler systems has been achieved. Oxidative aromatization reaction has been also realized by Pd-C/acetic acid/02 system. 1,3,5-Trisubstituted pyrazolines and Hantzsch 1,4-dihydropyridines were converted into the corresponding pyrazoles and pyridines effectively by the treatment of a catalytic amount of Pd/C in acetic acid under oxygen atmosphere. Direct synthesis of 2-arylbenzoxazoles from 2-aminophenols and aldehydes was achieved in the presence of activated carbon (Darco KB) under oxygen atmosphere. These environmentally benign oxidation methods have potentialities to replace the conventional stoichiometric chromium and other metal oxidizing agents.

Report

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

    (30 results)

All Other

All Publications (30 results)

  • [Publications] M.Hayashi: "Stereoselective C-Glycosidation of Unprotected D-Glycals with Trimethylsilyl Cyanide"Chirality. 15. 10-16 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.Kawashita: "Direct and Practical Synthesis of 2-Arylbenzoxazoles Promoted by Activated Carbon"Org.Lett.. 5. 3713-3715 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] N.Nakamichi: "Oxidative Aromatization of 1,3,5-Trisubstituted Pyrazolines and Hantzsch 1,4-Dihydropyridines by Pd/C in Acetic Acid"J.Org.Chem.. 68. 8272-8273 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] W.J.Drury: "Synthesis of Versatile Chiral N,P Ligands Derived from Pyridine and Quinoline"Angew.Chem.Int.Ed.. 43. 70-74 (2004)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Kawabata: "Lewis Base-Catalyzed Transformation of α,β-Unsaturated Aldehydes to Saturated Carboxylic Acids, Esters and Amides"Tetrahedron Lett.. 43. 5645-5647 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] N.Nakamichi: "Oxidative Aromatization of 1,3,5-Trisubstituted Pyrazolines and Hantzsch 1,4-Dihydropyridines by Pd/C in Acetic Acid"Org.Lett.. 4. 3955-3957 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] 林 昌彦: "第5版 実験化学講座 有機化合物の合成VII"丸善株式会社. 36 (2004)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Kawabata, M.Hayashi: "Benzylic Oxygenation of Alkylarenes with Molecular Oxygen in the Presence of Activated Carbon"Tetrahedron Lett.. (in press). (2004)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] N.Nakamichi, Y.Kawashita, M.Hayashi: "Activated Carbon-Promoted Oxidative Aromatization of Hantzsch 1,4-Dihydropyridines and 1,3,5-Trisubstituted Pyrazolines Using Molecular Oxygen"Synthesis. 1015-1020 (2004)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] W.J.Drury, N.Zimmermann, M.Keenan, M.Hayashi, S.Kaiser, R.Goddard, A.Pfaltz: "Synthesis of Versatile Chiral N, P Ligands Derived from Pyridine and Quinoline"Angew, Chem., Int.Ed.Eng.. 43. 70-74 (2004)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] N.Nakamichi, H.Kawabata, M.Hayashi: "Oxidative Aromatization of 9,10-Dihydroanthracenes Using Molecular Oxygen Promoted by Activated Carbon"J.Org.Chem.. 68. 8272-8273 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.Kawashita, N.Nakamichi, H.Kawabata, M.Hayashi: "Direct and Practical Synthesis of 2-Arylbenzoxazoles Promoted by Activated Carbon"Org.Lett.. 5. 3713-3715 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Hayashi, H.Kawabata, S.Nakayama: "Stereoselective C-Glycosidation of Unprotected D-Glycals with Trimethylsilyl Cyanide"Chirality, Special Issue : Dynamic Control of Stereochemistry.. 15. 10-16 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] N.Nakamichi, Y.Kawashita, M.Hayashi: "Oxidative Aromatization of 1,3,5-Trisubstituted Pyrazolines and Hantzsch 1,4-Dihydropyri dines by Pd/C in Acetic Acid"Org.Lett.. 4. 3955-3957 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Kawabata, M.Hayashi: "Lewis Base-Catalyzed Transformation of α,β-Unsaturated Aldehydes to Saturated Carboxylic Acids, Esters and Amides"Tetrahedron Lett.. 43. 5645-5647 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Hayashi, K.Yoshimoto, N.Hirata, K.Tanaka, N.Oguni, K.Harada, A.Matsushita, Y.Kawachi, H.Sasaki: "Enantioselective Addition of Diketene to Aldehydes Promoted by Chiral Schiff Base-Titanium Alkoxide Complex. Application to Asymmetric Synthesis of Potential Inhibitors of HMG Co-enzyme Reductase"Isr.J.Chem.. 41. 241-246 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Hayashi: "Stereoselective C-Glycosidation of Unprotected D-Glycals with Trimethylsilyl Cyanide"Chirality. 15. 10-16 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Y.Kawashita: "Direct and Practical Synthesis of 2-Arylbenzoxazoles Promoted by Activated Carbon"Org.Lett.. 5. 3713-3715 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] N.Nakamichi: "Oxidative Aromatization of 1,3,5-Trisubstituted Pyrazolines and Hantzsch 1,4-Dihydropyridines by Pd/C in Acetic Acid"J.Org.Chem.. 68. 8272-8273 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] W.J.Drury: "Synthesis of Versatile Chiral N, P Ligands Derived from Pyridine and Quinoline"Angew.Chem.Int.Ed.. 43. 70-74 (2004)

    • Related Report
      2003 Annual Research Report
  • [Publications] 林 昌彦: "第5版 実験化学講座 有機化合物の合成VII"丸善株式会社. 36 (2004)

    • Related Report
      2003 Annual Research Report
  • [Publications] M.Hayashi: "Enantioselective Addition of Diketene to Aldehydes Promoted by Chiral Schiff Basetitanium Alkoxide Complex Application to Asymmetric Synthesis of Potential Inhibitors of HMG Co-enzyme Reductase"Isr. J. Chem.. 41. 241-246 (2001)

    • Related Report
      2002 Annual Research Report
  • [Publications] 林 昌彦: "遷移金属触媒を用いたアルコールの環境適応型酸化反応"有機合成化学協会誌. 60. 137-144 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] H.Kawabata: "Lewis Base-Catalyzed Transformation of α,β-Unsaturated Aldehydes to Saturated Carboxylic Acids, Esters and Amides"Tetrahedron Lett.. 43. 5645-5647 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] N.Nakamichi: "Oxidative Aromatization of 1,3,5-Trisubstituted Pyrazolines and Hantzsch 1,4-Dihydropyridines by Pd/C in Acetic Acid"Org. Lett.. 4. 3955-3957 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] M.Hayashi: "Stereoselective C-Glycosidation of Unprotected D-Glycals with Trimethylsilyl Cyanide"Chirality. 15. 10-16 (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] 林 昌彦: "遷移金属触媒を用いたアルコールの環境調和型酸化反応"有機合成化学協会誌. 60. 137-144 (2002)

    • Related Report
      2001 Annual Research Report
  • [Publications] K.Yoshimoto: "Tris(2,4,6-trimethoxyphenyl)phosphine(TTMPP) : A Novel catalyst for Selective deacetylation"Chemistry Letters. 934-935 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] M.Hayashi: "Stereoselective synthesis of C-glycosides from D-glycals"Recent Res. Devel. Org. & Bioorg. Chem.. 4. 63-87 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] H.Kawabata: "Reaction of D-Glycals with Azidotrimethylsilane"Carbohydrate Res.. 333. 153-158 (2001)

    • Related Report
      2001 Annual Research Report

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

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