• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

Development of the novel C-C bond forming reactions using homogeneous transition metal catalysts

Research Project

Project/Area Number 09304069
Research Category

Grant-in-Aid for Scientific Research (A)

Allocation TypeSingle-year Grants
Section一般
Research Field 物質変換
Research InstitutionTOHOKU UNIVERSITY

Principal Investigator

YAMAMOTO Yoshinori  Graduate School of Science, Tohoku University, Professor, 大学院・理学研究科, 教授 (60029519)

Co-Investigator(Kenkyū-buntansha) SAITO Shinichi  Institute for Chemical Reaction Science, Tohoku University, Research Associate, 反応化学研究所, 助手 (80283076)
VLADIMIR Ger (GERORGYAW Vl)  東北大学, 大学院・理学研究科, 助教授 (80281971)
AL.MASUM Moh  東北大学, 反応化学研究所, 助手 (50282041)
Project Period (FY) 1997 – 1999
Project Status Completed (Fiscal Year 1999)
Budget Amount *help
¥40,500,000 (Direct Cost: ¥40,500,000)
Fiscal Year 1999: ¥3,500,000 (Direct Cost: ¥3,500,000)
Fiscal Year 1998: ¥5,500,000 (Direct Cost: ¥5,500,000)
Fiscal Year 1997: ¥31,500,000 (Direct Cost: ¥31,500,000)
KeywordsEnynes / Diynes / Alkynes / Palladium / Cycloaddition / Benzene / パラジウム触媒 / 共役エンイン / 芳香環化 / スチレン誘導体 / フェノール誘導体 / フラン誘導体 / シクロファン / ヘテロ環 / プロ求核剤 / アレン
Research Abstract

Monosubstituted conjugated enynes were found to undergo [4+2] homodimerization smoothly in the presence of palladium catalyst to give 4, α-and 2,6-disubstituted styrene derivatives. Analogous cross-cycloaddition of conjugated enynes and diynes was also developed to afford a variety of polysubstituted benzenes, including phenol and aniline derivatives. Alkynes and diynes in the presence of a palladium catalyst underwent novel formal [2+2+2] sequential cyclotrimerization to afford multifunctional benzenes in one step with high degrees of regio- and chemoselectivities. Mechanism of these novel transformations was proposed.

Report

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

    (46 results)

All Other

All Publications (46 results)

  • [Publications] J.-G.Shim,Y.Yamamoto: "A Novel and Effective Route to 1,3-Oxazolidine Derivatives. Palladium Catalyzed Regioselective[3+2]Cycloaddition of Vinylic Oxyranes with Imines"Tetrahedron Lett. 40. 1053-1056 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] S.Kamijo,Y.Yamamoto: "Synthesis of Cyclic Ethers via the Palladium Catalyzed Intramolecular Hydrocarbonation of Alkoxyallenes"Tetrahedron Lett. 40. 1747-1750 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] M.Meguro,Y.Yamamoto: "Novel Palladium Catalyzed Formal[3+2]Cycloaddition via Hydrocarbonation Reactions of Allenes"J.Org.Chem.. 64. 694-695 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] L.G.Quan,V.Gevorgyan,Y.Yamamoto: "Intramolecular Nucleophilic addition of Vinylpalladiums to Aryl Ketones"J.Am.Chem.Soc.. 121. 3545-3546 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] V.Gevorgyan,L.G.Quan,Y.Yamamoto: "Synthesis of Indenols and Indanones via Catalytic Cyclic Vinylpalladation of Aromatic Aldehydes"Tetrahedron Lett. 40. 4089-4092 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] V.Gevorgyan,Y.Yamamoto: "Palladium-catalyzed Enyne-yne[4+2]Benzannulation as a New and General Approach to Polysubstituted Benzenes"J.Organomet.Chem.. 576. 232-247 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Y.Yamamoto,U.Radhakrishnan: "Palladium Catalyzed Pronucleophile Addition to Unactivated Carbon-Carbon Multiple Bonds"Chem.Soc.Rev.. 28. 199-207 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] N.Tsukada,A.Shibuya,I.Nakamura,H.Kitahara,Y.Tamamoto: "Inter-and Intramolecular Palladium Catalyzed Hydrocarbonation of Methylenecyclopropanes with Carbon Pronucleophiles"Tetrahedron. 55. 8833-8844 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] V.Gevorgyan,A.Takeda,M.Homma,N.Sadayori,U.Radhakrishnan,Y.Yamamoto: "Palladium-Catalyzed[4+2]Cross-Benzannulation Reaction of Conjugated Enynes with Diynes and Triynes"J.Am.Chem.Soc.. 121. 6391-6402 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] I.Kadota,A.Shibuya,L.Lutete,Y.Yamamoto: "Palladium/Benzoic Acid Catalyzed Hydroamination of Alkynes"J.Org.Chem.. 64. 4570-4571 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] S.Saito,N.Tsuboya,Y.Chounan,T.Nagami,Y.Yamamoto: "Palladium-catalyzed Benzannulation of Conjugated Enynes. Enhanced Reactivity of Alkoxycarbonyl-and cyanoenynes"Tetrahedron Lett. 40. 7529-7532 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] D.H.Camacho,I.Nakamura,S.Saito,Y.Yamamoto: "Palladium-Catalyzed Hydroalkoxylation of Methylenecyclopropanes"Angew.Chem.Int.Ed.Engl.. 38. 3365-3367 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Y.Yamamoto: "Current Trends in Organic Synthesis"Academic/Plenum Pub.. 8 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] V.Gevorgyan,Y.Yamamoto: "Perspectives in Organopalladium Chemistry for the 21 Century"Elsevier. 16 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] J.-G.Shim, Y.Yamamoto: "A Novel and Effective Route to 1,3-Oxazolidine Derivatives. Palladium Catalyzed Regioselective [3+2] Cycloaddition of Vinylic Oxyranes with Imines"Tetrahedron Lett.. 40. 1053-1056 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] S.Kamijo, Y.Yamamoto: "Synthesis of Cyclic Ethers via the Palladium Catalyzed Intramolecular Hydrocarbonation of Alkoxyallenes."Tetrahedron Lett.. 40. 1747-1750 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] M.Meguro, Y.Yamamoto: "Novel Palladium Catalyzed Formal [3+2] Cycloaddition via Hydrocarbonation Reactions of Allenes."J. Org. Chem.. 64. 694-695 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] L.G.Quan, V.Gevorgyan. Y.Yamamoto: "Intramolecular Nucleophilic Addition of Vinylpalladiums to Aryl Ketones."J. Am. Chem. Soc.. 121. 3545-3546 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] V.Gevorgyan, L.G.Quan, Y.Yamamoto: "Synthesis of Indenols and Indanones via Catalytic Cyclic Vinylpalladation of Aromatic Aldehydes."Tetrahedron Lett.. 40. 4089-4092 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] V.Gevorgyan, Y.Yamamoto: "Palladium-catalyzed Enyne-yne [4+2] Benzannulation as a New and General Approach to Polysubstituted Benzenes."J. Organomet. Chem.. 576. 232-247 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Y.Yamamoto, U.Radhakrishnan: "Palladium Catalyzed Pronucleophile Addition to Unactivated Carbon-Carbon Multiple Bonds"Chem. Soc. Rev.. 28. 199-207 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] N.Tsukada, A.Shibuya, I.Nakamura, H.Kitahara, Y.Yamamoto: "Inter- and Intramolecular Palladium Catalyzed Hydrocarbonation of Methylenecyclopropanes with Carbon Pronucleophiles."Tetrahedron. 55. 8833-8844 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] V.Gevorgyan, A.Takeda, M.Homma, N.Sadayori, U.Radhakrishnan, Y.Yamamoto: "Palladium-Catalyze [4+2] Cross-Benzannulation Reaction of Conjugated Enynes with Diynes and Triynes."Am. Chem. Soc.. 121. 6391-6402 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] I.Kadota, A.Shibuya, L.Lutete, Y.Yamamoto: "Palladium/Benzoic Acid Catalyzed Hydroamination of Alkynes."J. Org. Chem.. 64. 4570-4571 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] S.Saito, N.Tsuboya, Y.Chounan, T.Nagami, Y.Yamamoto: "Palladium-catalyzed Benzannulation of Conjugated Enynes. Enhanced Reactivity of Alkoxycarbonyl- and cyanoenynes."Tetrahedron Lett.. 40. 7529-7532 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] D.H.Camacho, I.Nakamura, S.Saito, Y.Yamamoto: "Palladium-Catalyzed Hydroalkoxylation of Methylenecyclopropanes."Angew. Chem. Int. Ed. Engl.. 38. 3365-3367 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] J.-G.Shim,Y.Yamamoto: "A Novel and Effective Route to 1,3-Oxazolidine Derivatives. Palladium Catalyzed Regioselective [3+2] Cycloaddition of Vinylic Oxyranes with Imines"Tetrahedron Lett. 40. 1053-1056 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] S.Kamijo,Y.Yamamoto: "Synthesis of Cyclic Ethers via the Palladium Catalyzed Intramolecular Hydrocarbonation of Alkoxyallenes"Tetrahedron Lett. 40. 1747-1750 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] M.Meguro,Y.Yamamoto: "Novel Palladium Catalyzed Formal [3+2] Cycloaddition via Hydrocarbonation Reactions of Allenes"J. Org .Chem.. 64. 694-695 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] L.G.Quan,V.Gevorgyan,Y.Yamamoto: "Intramolecular Nucleophilic Addition of Vinylpalladiums to Aryl Ketones"J. Am. Chem. Soc.. 121. 3545-3546 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] V.Gevorgyan,L.G.Quan,Y.Yamamoto: "Synthesis of lndenols and Indanones via Catalytic Cyclic Vinylpalladation of Aromatic Aldehydes"Tetrahedron Lett. 40. 4089-4092 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] V.Gevorgyan,Y.Yamamoto: "Palladium-catalyzed Enyne-yne [4+2] Benzannulation as a New and General Approach to Polysubstituted Benzenes"J. Organomet .Chem.. 576. 232-247 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Y. Yamamoto: "Current Trends in Organic Synthesis"Academic/Plenum Pub.. 8 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] V. Gevorgyan, Y. Yamamoto: "Perspectives in Organopalladium Chemistry for the 21 Century"Elsevier. 16 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] 上條 真: "Palladium Latalyzed Hydrosulfination of Allenes with Tosylhydrnzine Leading to Allylsuttones" Telrahedron Letters. 39. 691-694 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Ukkiranapandian Radhakrishran: "Palladium Catulyzed Hydroamination of Conjugated Enynes" Tetrahedron Letters. 39. 1037-1040 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Douglas Weibel: "Synthesis of Polyethor Exomothylene Paracydophanes viaan Intranolecular Pd-Catalyzed Bis-Enyne Bnzannulation Protocol" The Journal of Orgaic Chemistry. 63. 1217-1220 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Vladimir Gerorgyan: "Regiospeccific Synthesis of Polysubstituted Phorols via the Palladium-Catalyzed Enyre-Diyne[4+2]Cross-Berzannulation Pathray" The Journal of Organic Chemistry. 63. 1244-1247 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Mohamnad Al-Masnm: "Pallndiua Cntalyzed Hydrocarboxylation of Allenes" The Journal of American Chemicul Society. 120. 3809-3810 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Vladinit Gerorgyan: "An Efficiout Route to 2,6-Disabstituted Styrenes vin the Palludium Catalyzed[4+2] Cyclodimerization of conjuguted Enynes" The Journal of Orgaric Chmistry. 63. 7022-7025 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] 斉藤慎一: "First Synthesis of Exomethylene Paracylophanes and Their Structural Properties" Journal of Organic Chemistry. 62. 5042-5047 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] 塚田直史: "Ring Opening in the Palladium Catalyzed Hydrocarbonation of Methylenecyeloprpanes with Pronuclehiles" Journal of American Chemical Society. 119. 8123-8124 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Vladimin Gevorgyan: "Palladium Catalyzed Addition of Carbon Pronucleophiles to Conjaguted Enynes" Tetrahedron. 53. 9097-9106 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] 塚田直史: "Intramolecular Hydrocarbonation of ε-Alkynic Malononitriles Catalyzed by Palladium Olefin Complexes" Angewandte Chemie,International Edition in English. 36. 2477-2480 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Vladimir Gerorgyan: "The First Chemo- and Regiospecific Palladium-Catalyzed Enyne-Diyne [4+2] Intramolecular Cross-Benzannulation : An Edfectire Route to Polysubstituted Benzenes" Tetrahedron Letters. 38. 8603-8604 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Vladimir Gevorgyan: "First Intramolecular Regiospecific Palladium-Catalyzed Enyne-Diyne [4+2] Cross-Benzannulation Reaction" Journal of American Chemical Society. 119. 11313-11314 (1997)

    • Related Report
      1997 Annual Research Report

URL: 

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

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi