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DEVELOPMENT OF HIGHLY EFFICIENT BENZYNE TRANSFORMATION PROCESS USING HYPERVALENT IODINE COMPOUNDS

Research Project

Project/Area Number 07804046
Research Category

Grant-in-Aid for Scientific Research (C)

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

Principal Investigator

KITAMURA Tsugio  KYUSHU UNIVERSITY,FACULTY OF ENGINEERING,ASSOCIATE PROFESSOR, 工学部, 助教授 (00153122)

Co-Investigator(Kenkyū-buntansha) FUJIWARA Yuzo  KYUSHU UNIVERSITY,FACULTY OF ENGINEERING,PROFESSOR, 工学部, 教授 (10029481)
Project Period (FY) 1995 – 1996
Project Status Completed (Fiscal Year 1996)
Budget Amount *help
¥2,300,000 (Direct Cost: ¥2,300,000)
Fiscal Year 1996: ¥900,000 (Direct Cost: ¥900,000)
Fiscal Year 1995: ¥1,400,000 (Direct Cost: ¥1,400,000)
KeywordsHypervalent Iodine Compounds / Benzyne / Iodonium Salts
Research Abstract

We have prepared a new type of hypervalent iodine reagent, [o-(trimethylsilyl) phenyl] iodonium triflates, which bear a hyperleaving phenyliodonio group and a readily cleavable silyl group, and developed a highly efficient benzyne transformation process.
(1) The benzyne precursor, [o-(trimethylsilyl) phenyl] iodonium triflate, was prepared by using highly reactive hypervalent iodine reagents developed by us.
(2) Benzyne was readily generated in situ under very mild conditions by using Bu_4NF and KF.
(3) The generated benzyne as above was quantitatively trapped by furan, isobenzofuran, anthracene, cyclopentadienone, and so on. This reaction provides a highly efficient benzyne transformation process.
(4) Since the present reagent can be utilized under neutral conditions and at room temperature, it can be applied to the reactions with unstable azides and thiobenzophenones.
(5) Substituted benzyne precursors were prepared and investigated in order to find the utility.

Report

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

    (21 results)

All Other

All Publications (21 results)

  • [Publications] 北村二雄: "[o- (Trimethylsilyl) phenyl] (phenyl) iodonium Triflate. A New and Efficient Precursor of Benzyne" Journal of Chemical Society,Chemical Communications. 983-984 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] 北村二雄: "Self-condensation of Iodosylbenzene. Formation of a p-Phenylene-type of Bisiodine (III) Reagents" Tetrahedron. 51. 6229-6236 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] 北村二雄: "高反応性有機ヨウ素(III)反応剤の開発" 有機合成化学協会誌. 53. 893-905 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] 北村二雄: "Coupling Reaction of Alkynyliodonium Salts with Alkynylcopper Reagents. A New Access to Liquid-Crystalline 1,3-Butadiynes" Mdecular Grystals and Liquid Crystals. 287. 93-100 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] 北村二雄: "Synthesis of Novel Vinylbenziodoxolones from Alkynyl (o-carboxyphenyl) iodonium Salts" Synlett. 659-660 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] 北村二雄: "An Efficient Ligand Exchange Reaction of β- (Trifyloxy) vinyliodonium Triflates with Aryllithium Reagents Leading to Diaryliodonium Triflates" Tetrahedron Letters. 37. 3721-3722 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] T.Kitamura and M.Yamane: "[o-(Trimethylsilyl) phenyl] (phenyl) iodonium Triflate. A New and Efficient Precursor of Benzyne" J.Chem.Soc., Chem.Commun.983-984 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] T.Kitamura, .K.Nagata, T.Nakamura, R.Furuki, and H.Taniguchi: "Selfcondensation of Iodosylbenzene. Formation of a p-Phenylene-type of Bisiodine (III) Reagents" Tetrahedron. 51. 6229-6236 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] T.Kitamura: "Reactive Organoiodine (III) Reagents : Synthesis and Applications" J.Synth.Org.Chem.Jpn.53. 893-905 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] T.Kitamura, C.H.Lee, Y.Taniguchi, Y.Fujiwara, Y.Sano, and M.Matsumoto: "Coupling Reaction of Alkynyliodonium Salts with Alkynylcopper Reagents. A New Access to Liquid-Crystalline 1,3-Butadiynes" Mol.Cryst.Liq.Cryst.287. 93-100 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] T.Kitamura, T.Fukuoka, and Y.Fujiwara: "Synthesis of Novel Vinylbenziodoxolones from Alkynyl (o-carboxyphenyl) iodonium Salts" Synlett. 659-670 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] T.Kitamura, M.Kotani, and Y.Fujiwara: "An Efficient Ligand Exchange Reaction of beta- (Trifyloxy) vinyliodonium Triflates with Aryllithium Reagents Leading to Diaryliodonium Triflates" Tetrahedron Lett.37. 3721-3722 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] 北村二雄: "Coupling Reaction of Alkynyliodonium Salts with Alkymylcopper Reagents.A New Access to Liquid-Crystalline 1,3-Butadiynes" Molecular Crystals and Liquid crystals. 287. 93-100 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] 北村二雄: "Synthesis of Novel Vinylbenziodoxolones from Alkynyl(o-carboxyphenyl)iodonium Salts" Synlett. 659-660 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] 北村二雄: "An Efficient Ligand Exchange Reaction of β-(Trifyloxy)vinyliodonium Triflates with Aryllithium Reagents Leading to Diaryliodonium Triflates" Tetrahedron Letters. 37. 3721-3722 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] 北村二雄: "A New Route to Chiral Diaryldiacetylenic Liquid Crystals.Preparation of Iodonium Salts Bearing Chiral Alkynyl Ligands and Utility for Chiral Alkynyl Transfer Agents" Journal of American Chemical Society. (印刷中). (1997)

    • Related Report
      1996 Annual Research Report
  • [Publications] 北村二雄 他2名: "A Novel Hypervalent Iodine Reagent Prepared from o-Iodosylbenzcic Acid and Trifluoromethanesulfanic Acid. Preparation and Reactions of Alkynyllo-(arboxyphenyl)-iodonium Triflates" Tetrahedron Letters. 36. 1081-1084 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] 北村二雄 他1名: "(Phenyl) [o-(trimethylsilyl) phenyl] iodonium Triflates. A New and Efficient Precursor of Benzyne" Journal of Chemical Society, Chemical Communications. 983-1984 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] 北村二雄 他4名: "Self-condensotion of Iodosylbenzene. Formation of a (p-Phenylene) Type of Bisiodine (III) Reagents" Tetrahedron. 51. 6229-6236 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] 北村二雄: "高反応性有機ヨウ素(III)反応剤の開発" 有機合成化学協会誌. 53. 893-905 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] 北村二雄 他6名: "Alkenyl-and Alkynyl-Substituted (p-Phenylene) bisiodonium Ditriflates by Reactions of a (p-Phenylene) bisiodine (III) Reagent with Alkynes and 1-Trimethylsilyl-1-alkynes" Bulletin of the Chemical Society of Japan. 68. 3637-3641 (1995)

    • Related Report
      1995 Annual Research Report

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

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