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The Development of Carbon-Carbon Bond Forming Process Using Aluminum Metal as A Electron Pool

Research Project

Project/Area Number 03555185
Research Category

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

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionOKAYAMA UNIVERSITY

Principal Investigator

TORII Sigeru  Okayama University・Department of Applied Chemistry, Professor, 工学部, 教授 (70032927)

Co-Investigator(Kenkyū-buntansha) INOKUCHI Tsutomu  Okayama University・Department of Applied Chemistry, Assistant Professor, 工学部, 助教授 (50168473)
OKUMOTO Hiroshi  Okayama University・Department of Applied Chemistry, Research Associate, 大学院・自然科学研究科, 助手 (90183251)
TANAKA Hideo  Okayama University・Department of Applied Chemistry, Assistant Professor, 工学部, 助教授 (60032950)
Project Period (FY) 1991 – 1993
Project Status Completed (Fiscal Year 1993)
Budget Amount *help
¥16,700,000 (Direct Cost: ¥16,700,000)
Fiscal Year 1993: ¥1,200,000 (Direct Cost: ¥1,200,000)
Fiscal Year 1992: ¥1,200,000 (Direct Cost: ¥1,200,000)
Fiscal Year 1991: ¥14,300,000 (Direct Cost: ¥14,300,000)
KeywordsAluminum Metal / Bimetal Redox / Carbon-Carbon Bond Forming Reaction / Selective Functional Group Transformation / beta-Lactam / Electron Transfer Catalyst / アルミニウム / 複合金属レドックス系 / 電子移動触媒系 / ポリハロアルカン / ビアツール / 炭素-炭素結合形成 / 特異的官能基変換 / ビアリール / ベーターラクタム / 3-ヒドロキシセフェム / 2-メチレンペナム
Research Abstract

Aluminum metal is an electron pool (reducing agent) which involves a lot of reactive electrons. We have demonstrated that a diverse transformation of functional groups and carbon-carbon bond forming reactions are selectively achieved by a new electron transfer process using aluminum metal as an electron source. In this project, we have investigated the following fundamental subjects in order to develop practical processes.
(a) The electron transfer process from the surface of aluminum metal is highly dependent on the solvent, another redox metal, and additives. We have studied the bimetal redox system to realize the most efficient electron transfer system for the purposes.
(b) Some multi metal redox systems consisting of transition metal, reducing metal, and electron pool metal have been found to achieve a variety of organic reactions involving carbon-carbon bond formation. As an example, a facile coupling reaction of alkenyl halides leading to dienes was developed.
(c) The redox systems have been applied to the transformation of beta-lactam compounds and new practical synthetic processes of the antibiotics have been developed.

Report

(4 results)
  • 1993 Annual Research Report   Final Research Report Summary
  • 1992 Annual Research Report
  • 1991 Annual Research Report
  • Research Products

    (32 results)

All Other

All Publications (32 results)

  • [Publications] S.Torii: "Carbonylative[2+2]Cycloaddition for the Construction of β-Lactam Skeleton with Palladium Catalyst" TETRAHEDRON LETT.34. 6553-6556 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] S.Torii: "A Facile Conversion of 2-Substituted Acrylamides to 1,3-Disubstituted 3-Bromo-2-Azetidinones" SYNTH.COMMUN.23. 517-523 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] S.Torii: "Palladium-Catalyzed Sequential Bond Formation Leading to Conjugated Ene-Yne System" TETRAHEDRON LETT.34. 2139-2142 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] H.Tanaka: "Mg/PbBr_2 Bimetal Redox-Promoted Stannation of Propargyl,Allyl,Vinyl,and Aryl Halides" Synlett. 835-836 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] H.Tanaka: "2-Substituted Penems,New Candidates for Cephalosporinase Inhibitors" Bioorganic & Medicinal Chemistry Letters. 3. 2253-2254

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] T.Inokuchi: "Electrochemical Wacker Type Reaction with a double Mediatory System Consisting of Palladium Complex and Tri(4-bromophenyl)amine" Chemistry Letter. 121-124

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] S.Torii, H.Okumoto, T.Tadokoro, A.Nishimura and M.A.Rashid: "Palladium-Catalyzed Sequential Bond Formation Leading to Conjugated Ene-Yne System" TETRAHEDRON LETT.Vol 34, No.13. 2139-2142 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] S.Torii, H.Okumoto and H.Yabuki: "A Facile Conversion of 2-Substituted Acrylamides to 1, 3-Disubstituted 3-Bromo-2-Azetidinones" SYNTH.COMMUN.23(4). 517-523 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] S.Torii, H.Okumoto, M.Sadakane, A.K.M.Abdul Hai and H.Tanaka: "Carbonylative [2+2] Cycloaddition for the Construction of beta-Lactam Skeleton with Palladium Catalyst" TETRAHEDRON LETT.Vol 34, No.41. 6553-6556 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] H.Tanaka, Y.Kameyama, S.Sumida, and S.Torii: "2-Substituted Penems, New Candidates for Cephalosporinase Inhibitors" Bioorganic & Medicinal Chemistry Letters. Vol.3, No.11. 2253-2254 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] H.Tanaka, A.K.M.A.Hai, H.Ogawa, and S.Torii: "Mg/PbBr_2 Bimetal Redox-Promoted Stannation of Propargyl, Allyl, Vinyl, and Aryl Halides" Synlett. No.11. 835-836 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] T.Inokuchi, K.Ping, F.Hamaue, M.Izawa, and S.Torii: "Electrochemical Wacker Type Reaction with a double Mediatory System Consisting of Palladium Complex and Tri(4-bromophenyl)amine" Chemistry Letter. 121-124 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] S.Torii: "Carbonylative[2+2]Cycloaddition for the Construction of β-Lactam Skeleton with Palladium Catalvst" TETRAHEDRON LETT.34. 6553-6556 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] S.Torii: "A Facile Conversion of 2-Substituted Acrylamides to 1,3-Disubstituted 3-Bromo-2-Azetidinones" SYNTH.COMMUN.23. 517-523 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] S.Torii: "Palladium-Catalyzed Sequential Bond Formation Leading to Conjugated Ene-Yne System" TETRAHEDRON LETT.34. 2139-2142 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] H.Tanaka: "Mg/PbBr_2 Bimetal Redox-Promoted Stannation of Propargyl,Allyl,Vinyl,and Aryl Halides" Synlett. 835-836 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] H.Tanaka: "2-Substituted Penems,New Candidates for Cephalosporinase Inhibitors" Bioorganic & Medicinal Chemistry Letters. 3. 2253-2254 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] T.Inokuchi: "Electrochemical Wacker Type Reaction with a double Mediatory System Consisting of Palladium Complex and Tri(4-bromophenyl)amine" Chemistry Letter. 121-124 (1994)

    • Related Report
      1993 Annual Research Report
  • [Publications] Tsutomu Inokuchi: "Indirect Electrooxidation of Alcohols by a Double Mediatory System with Two Redox Couples of [R_2N^+=O]/R_2NO and [Br or Br^+]/Br^- in an Organic-Aqueous Two-Phase Solution" Journal of Organic Chemistry. 56. 2416-2421 (1991)

    • Related Report
      1992 Annual Research Report
  • [Publications] Tsutomu Inokuchi: "Electrohalogenation of Propargyl Acetates and Amides to Form 1,1-Dibromo-2-oxo Functionality and a Facile Synthesis of Fucaneol" Journal of Organic Chemistry. 57. 5023-5027 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Sigeru Torii: "Asymmertric Multipoint Control by Palladium-catalyzed Diastereoselective Tandem Carbon-Carbon Bond Formation" Tetrahedron Letters. 33. 3503-3506 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Sigeru Torii: "Asymmertric Multipoint Control by Diastereo-Differentiative Assembly of Three Components with Palladium Catalyst" Tetrahedron Letters. 33. 3499-3502 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Hideo Tanaka: "A Facile Synthesis of C(3)-Alkenyl Substituted Cephems through Addition-Cyclization of Allenecarboxylates derived from Penicillin^1" Tetrahedron Letters. 46. 7029-7030 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Hideo Tanaka: "A Facile Synthesis of 2-exo-Methylenepenam through Reductive Cyclization of Allenecarboxylates in a Metal Salt/Metal Bimetal Redox System" SYNLETT. 878-880 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Hideo Tanaka: "A Convenient Synthesis of 2-exo-Methylene Penam,A Potent Intermediate for New β-Lactam Antibiotics Synthesis" Tetrahedron Letters. 32. 7445-7448 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Tsutomu Inokuchi: "Vanadium(II)-Promoted Cyclization of 5,6-Enals or 5,6-Ynals.A Stereo-selective Approach to trans-2-Alkyl or 2-Alkylidenecyclopentanols" The Journal Organic Chemistry. 56. 4983-4985 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Tsutomu Inokuchi: "Indirect Electroreduction of 2-Alkyl-2-(bromomethyl)alkanones with Cobaloxime to Form 3-Alkyl-2-alkenones via 1,2-Acyl Migration" The Journal Organic Chemistry. 56. 5945-5948 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Sigeru Torii: "A Convenient Approach to 1,4-Dihydro-4-oxo-3-quinoline Carboxylates by Electro-Oxidative Formation of Enamine Moiety" Tetrahedron. 47. 665-674 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Sigeru Torii: "Palladium-Catalyzed Tandem Bond Forming Reaction Leading to Aromatic Ring Through Diene-Yne System" Tetrahedron Letters. 32. 4167-4168 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Hideo Tanaka: "A Convenient Access to 2-exo-Methylenecephem" Synlett. (1992)

    • Related Report
      1991 Annual Research Report
  • [Publications] Sigeru Torii,Hideo Tanaka(分担): "Organic Electrochemistry.An Introduction and a Guide" Marcel Dekker,Inc, 45 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Sigeru Torii: "Comprehensive Organic Synthesis" Pergamon Press plc, 14 (1991)

    • Related Report
      1991 Annual Research Report

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Published: 1991-04-01   Modified: 2016-04-21  

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