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Development of Novel Synthetic Reactions Based on the Activation of the Third Row Elements'

Research Project

Project/Area Number 07405042
Research Category

Grant-in-Aid for Scientific Research (A)

Allocation TypeSingle-year Grants
Section一般
Research Field Synthetic chemistry
Research InstitutionKYOTO UNIVERSITY (1997-1998)
Tokyo Institute of Technology (1995-1996)

Principal Investigator

HIYAMA Tamejiro  Kyoto University Graduate School of Engineering Professor, 工学研究科, 教授 (90026295)

Co-Investigator(Kenkyū-buntansha) SHIMIZU Masaki  Kyoto University Graduate School of Engineering Instructor, 工学研究科, 助手 (10272709)
白川 英二  京都大学, 工学研究科, 助手 (70273472)
Project Period (FY) 1995 – 1998
Project Status Completed (Fiscal Year 1998)
Budget Amount *help
¥33,300,000 (Direct Cost: ¥33,300,000)
Fiscal Year 1998: ¥4,000,000 (Direct Cost: ¥4,000,000)
Fiscal Year 1997: ¥3,900,000 (Direct Cost: ¥3,900,000)
Fiscal Year 1996: ¥8,800,000 (Direct Cost: ¥8,800,000)
Fiscal Year 1995: ¥16,600,000 (Direct Cost: ¥16,600,000)
KeywordsOxidative Desulfurization-Fluorination / Organofluorine Compounds / Organosiliocn Compounds / Cross Coupling Reaction / Transmetalation / Carbostannylation / Trifluoromethylation / palladium Catalyst / シラノール / パラジウム / 銅 / ジフルオロオレフィン / フルオロプーメラ転位 / 有素ケイ素化合物 / 塩化アリール / 有機フッ素化合物 / 酸化的脱硫フッ素化 / キサントゲン酸エステル / トリフルオロメチルエーテル / ビニルエポキシド / 水酸化ナトリウム / 環状アリルシラン / フッ化物イオン / フルオロプ-メラ-転位 / 不斉クロスカップリング反応 / 光学活性アリルシラン / 不斉転写 / トリフルオロメチルアミン型液晶化合物
Research Abstract

(1) Oxidative Desulfurization Fluorination
Upon reaction with an oxidant like a positive halogen, organosulfur compounds gives sulfonium ions whose C-S bonds are weaked to undergo nucleophilic substitution readily. A fluoride ion of 70% HF/Py and Bu_4NH_2F_3 replaces sulfur to give organofluorine compounds. In this way, trifluoromethyl-substituted aromatics and olefins, trifluoromethyl ethers, trifluoromethylamines, alpha-fluoro sulfides, and vis-difluoro olefins are shown to be readily available from the corresponding organosulfur precursors.
(2) Cross-Coupling Reactions with Organosilicon Compounds
This novel reaction is now called as the Hiyama Coupling. Although a trimethylsilyl group is pertinent to vinylsilanes, SiFMe_2 or SiF_2 Me is necessary for alkenylsilanes in general.
Alkoxysilanes also are applicable. As a coupling partner, aryl chlorides are now shown to be applicable.
Transmetalation from silicon to copper(I) is now achieved in DMF.Thus, alkynylsilanes couple with halobenzenes or dimerizes oxidatively using a palladium catalyst. Conjugate reduction of alpha, beta-unsaturated esters and ketones is attained with hydrosilanes.
(3) Cross-Coupling and Carbostannylation with Organotin Compounds
Using a novel catalyst consisting of palladium and an imino phosphine ligand, organotin compounds are shown to readily undergo cross-coupling reactions, oxidative dimerization, and carbostannylation to acetylenes.

Report

(5 results)
  • 1998 Annual Research Report   Final Research Report Summary
  • 1997 Annual Research Report
  • 1996 Annual Research Report
  • 1995 Annual Research Report
  • Research Products

    (128 results)

All Other

All Publications (128 results)

  • [Publications] M.Kuroboshi: "Synthesis of Trifluoromethylamino-Substituted Pyridines and Pyrimidines by Oxidative Desulfurization-Fluorination" Tetrahedron Lett.36(4). 563-566 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] H.Matsuhashi: "Palladium-Catalyzed Cross-Coupling of Allylic Carbonates with Alkenylfluorosilanes in the Absence of Fluoride Ion" Tetrahedron Lett.36(9). 1539-1540 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Kuroboshi: "Halofluorination of Alkenes Using Dilute Hydrofluoric Acid" Bull.Chem.Soc.Jpn.68. 1799-1805 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] K.Kanie: "Synthesis and Properties of New Liquid Crystals Containing Trifluoromethylamino Group" Chem.Lett.683-684 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] K.Takahashi: "Synthesis of an Artificial HMG-CoA Reductase Inhibitor NK-104 via a Hydrosilylation-Cross-coupling Reaction" Bull.Chem.Soc.Jpn.68. 2649-2656 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] H.Ohmura: "Catalytic Asymmetric Hydrosilylation of 1,3-Dienes with Difluoro(phenyl)silane" J.Organometal.Chem.499. 167-171 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] E.Hagiwara: "Allylation of Quinones with Allyl(trifluoro)silanes : Direct Synthesis of Isoprenoid Quinones" Tetrahedron Lett.36(16). 2773-2776 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] H.Sugita: "Silylation of 1-Alkynes with Chlorosilanes Promoted by Zinc : Preparation of Alkynylsilanes in a Single Step" Tetrahedron Lett.36(16). 2769-2772 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Kuroboshi: "Oxidative Desulfurization-Fluorination of 1-Substituted 2,2,2-Tri(methylthio)ethanol Induces Difluorination under Oxidation or Rearrangement" Tetrahedron Lett.36. 6121-6122 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] S.Furuta: "Fluoro-Pummerer Rearrangement under Oxidative Desulfurization Fluorination Conditions. Facile Syntheses of Oligofluoroalkyl Sulfides" Tetrahedron Lett.36(45). 8243-8246 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] H.Matsuhashi: "Synthesis of 5-Substituted Pyrimidine Nucleosides Through a Palladium-Catalyzed Cross-Coupling of Alkenylhalosilanes" Heterocycles. 42(1). 375-384 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] H.Sugita: "A Convenient Synthesis of Alkynylsilanes by Silylation of Copper(I)Alkynides" Chem.Lett.379-380 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] K.Goda: "Cross-Coupling Reactions of Aryl Chlorides with Organochlorosilanes : Highly Effective Methods for Arylation or Alkenylation of Aryl Chlorides" J.Org.Chem.61(21). 7232-7233

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] S.Furuta: "Difluorination of 2-Substituted 1,1,1-Tris(methylthio)ethanes by Oxidative Desulfurization-Fluorination. A New Route to Partially Fluorinated Olefins" Tetrahedron Lett.37(44). 7983-7986 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] T.Hiyama: "Chirality Transfer via the Palladium-Catalyzed Cross-Coupling Reaction of Optically Active 2-Cyclohexenylsilane : Stereochemical and Mechanistic Aspects" Organometallics. 15(26). 5762-5765 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] S.Furuta: "A Facile Synthesis of Substituted 3,3,3-Trifluoropropenes by Oxidative Desulfurization-Fluorination of the Corresponding dithiopropenoates" Synlett,. 1996(12). 1199-1200

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] E.Hagiwara: "NaOH-Promoted Cross Coupling Reactions of Organosilicon Compounds with Organic Halides : Practical Routes to Biaryls, Alkenylarenes and Conjugated Dienes" Tetrahedron Lett.38(3). 439-442 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] H.Matsuhashi: "Palladium-Catalyzed Cross-Coupling Reaction of Alkyltrifluorosilanes with Aryl Halides" Bull.Chem.Soc.Jpn.70(2). 437-444 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] K.Kanie: "Oxidative Desulfurization-Fluorination of Alkanol Xanthates. Control of the Reaction Pathway to Fluorination or Trifluoromethoxylation" Chem.Commun.1997(3). 309-310

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] K.Ikegashira: "Copper(I) Salt Promoted Homo-coupling Reaction of Organosilanes." Chem.Commun.1997(6). 1039-1040

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] K.Kanie: "Synthesis and Electro-optical Properties of Novel Liquid Crystals Having a Cyclohexyl Trifluoromethyl Ether Moiety" Chem.Lett.1997. 827-828

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] H.Matsuhashi: "The Palladium-Catalyzed Cross-Coupling Reaction of Organosilicon Compounds with Allylic Carbonates or Diene Monoxidess" Bull.Chem.Soc.Jpn.70. 1943-1952 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] A.Mori: "TBAHF_2 and TBAH_2F_3 as Activating Agents of Organosilanes" Synlett,. 1997(6). 639-694 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] E.Shirakawa: "On the Catalytic Cycle of the Palladium-Catalyzed Cross-Coupling Reaction of Alkynylstannane with aryl Iodide" Tetrahedron Lett.38(29). 5177-5180 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Y.Nishihara: "Cu(I)/Pd(0)-Catalyzed Cross-Coupling Reaction of Alkynylsilanes with Aryl or Alkenyl Triflates : ““Sila""-Sonogashira-Hagihara Coupling" Chem.Lett.1997(12). 1233-1234

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] E.Shirakawa: "Homocoupling of Organostannanes Catalyzed by Iminophosphine-Palladium" Synlett,. 1997(10). 1143-1144

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] E.Shirakawa: "Nickel-catalysed Cross-coupling Reactions of Aryl Halides with Organostannanes" J.Chem.Soc., Perkin Trans. 1. 1997. 2449-2450

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] A.Mori: "Copper(I) Salt Mediated 1,4-Reduction of α,β-Unsaturated Ketones Using Hydrosilanes" Chem.Commun. 1997(22). 2159-2160

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] E.Shirakawa: "Carbostannylation of Alkynes Catalyzed by an Iminophosphine-alladium Complex" Am.Chem.Soc.120. 2975-2976 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Y.Nishihara: "Copper(I)-Catalyzed Cross-Coupling Reaction of Alkynylsilanes with 1-Chloroalkynes" Tetrahedron Lett.39. 4075-4078 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] S.Furuta: "Fluorination of Orthothioesters through Oxidative Desulfurization - luorination" Bull.Chem.Soc.Jpn.71(8). 1939-1951 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] K.Kanie: "A Facile Synthesis of Trifluoromethylamines by Oxidative Desulfurization-Fluorination of Dithiocarbamates" Bull.Chem.Soc.Jpn.71(8). 1973-1991 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] K.Kanie: "A Facile Synthesis and Electro-optical Properties of New Liquid Crystals Having a vic-Difluoro Olefinic Moiety" Chem.Lett.1998. 1169 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] S.Furuta: "Facile Synthesis of α-Fluoroalkyl Sulfides under the Oxidative Desulfurization-Fluorination Conditions" Bull.Chem.Soc.Jpn.71(11). 2687-2694 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] K.Hirabayashi: "A Novel C-C Bond Forming Reaction of Aryl- and Alkenylsilanols. A Halogen-Free Mizoroki-Heck Type Reaction" Tetrahedron Lett.39. 7893-7896 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] E.Shirakawa: "Cross-Coupling Reaction of Organostannanes with Aryl Halides Catalyzed by Nickel-Triphenylphosphine or Nickel-Lithium Halide Complex" Synthesis. 1998(10). 1544-1549 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] 檜山爲次郎: "液晶材料の有機合成化学" 日本学術振興会創造機能化学第116委員会業績報告. 48. 161 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] 杉田 光: "亜鉛を用いる1-アルキンのシリル化反応とポリマー合成への応用" 日本学術振興会創造機能化学第116委員会業績報告. 48. 212 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] 檜山爲次郎: "有機ケイ素化合物の新しい活性化に基づくカップリング反応" 日本学術振興会創造機能化学第116委員会業績報告. 49. 57 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] 檜山爲次郎: "銅(I)塩を用いる有機ケイ素のカップリング反応 : 新しい炭素-炭素結合生成反応" 日本学術振興会創造機能化学第116委員会業績報告. 50. 231 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] 白川英二: "パラジウム-イミノホスフィン触媒を用いる有機スズ化合物の反応" 有機合成化学協会誌. 56(10). 810-817 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] H.Sugita: "A Novel Reduction of Zinc(II) Chloride with Samarium Metal and its Application to Silylation of 1-Alkynes" Synlett,. 1996. 637-638 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] T.Hiyama: "Metal-catalyzed Cross-coupling Reactions in Metal-catalyzed Cross-coupling Reactions, Chapter 10" Ed.by F.Diederich and P.J.Stang, Wiley-VCH, 33 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Kuroboshi: "Synthesis of Trifluoromethylamino-Substituted Pyridines and Pyrimidines by Oxidative Desulfurization-Fluorination" Tetrahedron Lett.36(4). 563-566 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] H.Matsuhashi: "Palladium-Catalyzed Cross-Coupling of Allylic Carbonates with Alkenylfluorosilanes in the Absence of Fluoride Ion" Tetrahedron Lett.36(9). 1539-1540 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Kuroboshi: "Halofluorination of Alkenes Using Dilute Hydrofluoric Acid" Bull.Chem.Soc.Jpn.68. 1799-1805 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] K.Kanie: "Synthesis and Properties of New Liquid Crystals Containing Trifluoromethylamino Group" Chem.Lett.683-684 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] K.Takahashi: "Synthesis of an Artificial HMG-CoA Reductase Inhibitor NK-104 via a Hydrosilylation-Cross-coupling Reaction" Bull.Chem.Soc.Jpn.68. 2649-2656 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] H.Ohmura: "Catalytic Asymmetric Hydrosilylation of 1,3-Dienes with Difluoro (phenyl) silane" J.Organometal.Chem.499. 167-171 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] E.Hagiwara: "Allylation of Quinones with Allyl (trifluoro) silanes : Direct Synthesis of Isoprenoid Quinones" Tetrahedron Lett.36(16). 2773-2776 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] H.Sugita: "Silylation of 1-Alkynes with Chlorosilanes Promoted by Zinc : Preparation of Alkynylsilanes in a Single-Step" Tetrahedron Lett.36(16). 2769-2772 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Kuroboshi: "Oxidative Desulfurization-Fluorination of 1-Substituted 2,2,2-Tri (methylthio) ethanol Induces Difluorination under Oxidation or Rearrangement" Tetrahedron Lett.36(34). 6121-6122 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] S.Furuta: "Fluoro-Pummerer Rearrangement under Oxidative Desulfurization Fluorination Conditions. Facile Syntheses of Oligofluoroalkyl Sulfides" Tetrahedron Lett.36(45). 8243-8246 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] H.Matsuhashi: "Synthesis of 5-Substituted Pyrimidine Nucleosides Through a Palladium-Catalyzed Cross-Coupling of Alkenylhalosilanes" Heterocycles. 42(1). 375-384 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] H.Sugita: "A Convenient Synthesis of Alkynylsilanes by Silylation of Copper (I) Alkynides" Chem.Lett.379-380 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] K.Goda: "Cross-Coupling Reactions of Aryl Chlorides with Organochlorosilanes : Highly Effective Methods for Arylation or Alkenylation of Aryl Chlorides" J.Org.Chem.61(21). 7232-7233

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] S.Furuta: "Difluorination of 2-Substituted 1,1,1-Tris (methylthio) ethanes by Oxidative Desulfurization-Fluorination. A New Route to Partially Fluorinated Olefins" Tetrahedron Lett.37(44). 7983-7986 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] T.Hiyama: "Chirality Transfer via the Palladium-Catalyzed Cross-Coupling Reaction of Optically Active 2-Cyclohexenylsilane : Stereochemical and Mechanistic Aspects" Organometallics. 15(26). 5762-5765 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] S.Furuta: "A Facile Synthesis of Substituted 3,3,3-Trifluoropropenes by Oxidative Desulfurization-Fluorination of the Corresponding dithiopropenoates" Synlett. 1996(12). 1199-1200

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] E.Hagiwara: "NaOH-Promoted Cross Coupling Reactions of Organosilicon Compounds with Organic Halides : Practical Routes to Biaryls, Alkenylarenes and Conjugated Dienes" Tetrahedron Lett.38(3). 439-442 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] H.Matsuhashi: "Palladium-Catalyzed Cross-Coupling Reaction of Alkyltrifluorosilanes with Aryl Halides" Bull.Chem.Soc.Jpn.70(2). 437-444 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] K.Kanie: "Oxidative Desulfurization-Fluorination of Alkanol Xanthates. Control of the Reaction Pathway to Fluorination or Trifluoromethoxylation" Chem.Commun.1997(3). 309-310

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] K.Ikegashira: "Copper (I) Salt Promoted Homo-coupling Reaction of Organosilanes" Chem.Commun.1997(6). 1039-1040

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] K.Kanie: "Synthesis and Electro-optical Properties of Novel Liquid Crystals Having a Cyclohexyl Trifluoromethyl Ether Moiety" Chem.Lett.1997. 827-828

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] H.Matsuhashi: "The Palladium-Catalyzed Cross-Coupling Reaction of Organosilicon Compounds with Allylic Carbonates or Diene Monoxides" Bull.Chem.Soc.Jpn.70. 1943-1952 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] A.Mori: "TBAHF_2 and TBAH_2F_3 as Activating Agents of Organosilanes" Synlett. 1997(6). 693-694 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] E.Shirakawa: "On the Catalytic Cycle of the Palladium-Catalyzed Cross-Coupling Reaction of Alkynylstannane with ary Iodide" Tetrahedron Lett.38(29). 5177-5180 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Y.Nishihara: "Cu (I) /Pd (0) -Catalyzed Cross-Coupling Reaction of Alkynylsilanes with Aryl or Alkenyl Triflates : ""Sila"" -Sonogashira-Hagihara Coupling" Chem.Lett.1997(12). 1233-1234

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] E.Shirakawa: "Homocoupling of Organostannanes Catalyzed by Iminophosphine-Palladium" Synlett. 1997(10). 1143-1144

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] E.Shirakawa: "Nickel-catalysed Cross-coupling Reactions of Aryl Halides with Organostannanes" J.Chem.Soc, Perkin Trons.1. 2449-2450 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] A.Mori: "Copper (I) Salt Mediated 1,4-Reduction of alpha, beta-Unsaturated Ketones Using Hydrosilanes" Chem.Commun.1997(22). 2159-2160

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] E.Shirakawa: "Carbostannylation of Alkynes Catalyzed by an Iminophosphine-Palladium Complex" J.Am.Chem.Soc.120. 2975-2976 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Y.Nishihara: "Copper (I) -Catalyzed Cross-Coupling Reaction of Alkynylsilanes with 1-Chloroalkynes" Tetrahedron Lett.39. 4075-4078 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] S.Furuta: "Fluorination of Orthothioesters through Oxidative Desulfurization-Fluorination" Bull.Chem.Soc.Jpn.71(8). 1939-1951 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] K.Kanie: "A Facile Synthesis of Trifluoromethylamines by Oxidative Desulfurization-Fluorination of Dithiocarbamates" Bull.Chem.Soc.Jpn.71(8). 1973-1991 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] K.Kanie: "A Facile Synthesis and Electro-optical Properties of New Liquid Crystals Having a vic-Difluoro Olefinic Moiety" Chem.Lett.1998. 1169

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] S.Furuta: "Facile Synthesis of a-Fluoroalkyl Sulfides under the Oxidative Desulfurization-Fluorination Conditions" Bull.Chem.Soc.Jpn.71(11). 2687-2694 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] K.Hirabayashi: "A Novel C-C Bond Forming Reaction of Aryl-and Alkenylsilanols. A Halogen-Free Mizoroki-Heck Type Reaction" Tetrahedron Lett.39. 7893-7896 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] E.Shirakawa: "Cross-Coupling Reaction of Organostannanes with Aryl Halides Catalyzed by Nickel-Triphenylphosphine or Nickel-Lithium Halide Complex" Synthesis. 1998(10). 1544-1549

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] H.Hiyama: "Organic Synthesis of Liquid Crystalline Materials" JSPS,the 116th Committee Report. 48. 161 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] H.Sugita: "Silylation of 1-Alkynes with Zinc and Application to Polymer Synthesis" JSPS,the 116th Committee Report. 48. 212 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] T.Hiyama: "Coupling Reactions Based on Novel Activation of Organosilicon Compounds" JSPS,the 116th Committee Report. 49. 57 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] T.Hiyama: "Coupling Reactions of Organosilicon Compounds with Cu (I) : Novsel Carbon-Carbon Bond Formation Reactions" JSPS,the 116th Committee Report. 50. 231 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] E.Shirakawa: "Synthetic Reactions of Organotin Compounds using a Palladium-Imino Phosphine Catalyst" Yuki Gosei Kagaku Kyokai Shi. 56(10). 810-817 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] H.Sugita: "A Novel Reduction of Zinc (II) Chloride with Samarium Metal and its Application to Silylation of 1-Alkynes" Synlett. 1996. 637-638 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] E.Shirakawa: "Carbostannylation of alkynes catalyzed by an iminophosphine-palladium complex" J.Am.Chem.Soc.120(12). 2975-2976 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Y.Nishihara: "Copper(I)-catalyzed cross-coupling reaction of alkynylsilanes with 1-chloroalkynes" Tetrahedron Lett.39. 4075-4078 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] S.Furuta: "Fluorination of orthothioesters through oxidative desulfurization-fluorination" Bull.Chem.Soc.Jpn.71. 1939-1951 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] K.Kanie: "A facile synthesis of trifluoromethylamines by oxidative desulfurization-fluorination of dithiocarbamates" Bull.Chem.Soc.Jpn.71. 1973-1991 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] K.Kanie: "A facile synthesis and electro-optical properties of new liquid crystals having a vic-difluoro olefinic moiety" Chem.Lett.1169-1170 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] S.Furuta: "Facile synthesis of a-fluoroalkyl sulfides under the oxidative desulfurization-fluorination conditions" Bull.Chem.Soc.Jpn.71. 2687-2694 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] K.Hirabayashi: "A novel C-C bond forming reaction of aryl-and alkenylsilanols. A halogen-free Mizoroki-Heck type reaction" Tetrahedron Lett.39. 7893-7896 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] E.Shirakawa: "Cross-coupling reaction of organostannanes with aryl halides catalyzed by nickel-triphenylphosphine or nickel-lithium halide complex" Synthesis. 1544-1549 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] 白川英二: "パラジウム-イミノホスフィン触媒を用いる有機スズ化合物の反応" 有機合成化学協会誌. 56(10). 810-817 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] 桧山爲次郎: "A Facile Synthesis of Substituted 3,3,3-Trifluoropropene.S by oxidative Desulfurl zation-Flouorination of the Corresponding dithiopropenoate" Synlett. 12. 1199-1200 (1996)

    • Related Report
      1997 Annual Research Report
  • [Publications] 桧山爲次郎: "NaoH-promoted Cross-Coupling Reactions of Organosilicon Compounds with Organic Halides : Practical Routes to Biaryls,Alkenylarenes and Conjugated Dienes" Tetrahedron Lett. 38・3. 439-442 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] 桧山爲次郎: "Palladium-Catalyzed Cross-Coupling Reaction of Alkyltrifluorosilanes with Aryl Halides" Bull.Chem.Soc.JPn. 70・2. 437-444 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] 桧山爲次郎: "Oxidative Desulfurization-Fluorination of Alkanol Xanthates.Control of the Reaction Pathway to Fluorination or Trifluoromethoxylation" Chem.Commun. 3. 309-310 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] 桧山爲次郎: "Copper (I) Salt Promoted Homo-coupling Reaction of Organosilanes" Chem.Commun. 6. 1039-1040 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] 桧山爲次郎: "Synthesis and Electro-Optical Properties of Novel Liquid Crystals Having a Cyclohexyl Trifluoromethyl Ether Moiety" Chem.Lett. 827-828 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] 桧山爲次郎: "The Palladium-Catalyzed Cross-Coupling Reaction of Organosilicon Compounds with Allylic Carbonates or Diene Monoxi" Bull.Chem.Soc.Jpn. 70. 1943-1952 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] 桧山爲次郎: "TBAHF_2 and TBAH_2F_3 as Activating of Organosilanes Agents." Synlett. 6. 693-694 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] 桧山爲次郎: "On the Catalytic Cycle of the Palladium-Catalyzed Cyoss-Coupling Reaction of Alkynylstannane with aryl Iodide." Tetrahedron Lett. 38・29. 5177-5180 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] 桧山爲次郎: "Cu (I) /Pd (O) -Catalyzed Cross-Coupling Reaction of Alkynylsilan with Aryl or Alkenyl Triflates : "Sila"-Sonogashira-Hagihara Coupling" Chem.Lett. 12. 1233-1234 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] 桧山爲次郎: "Homocoupling of Organostannanes Catalyzed by Iminophosphine-Palladium" Synlett. 10. 1143-1144 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] 桧山爲次郎: "Nickel-Catalysed Cross-Couplig Reactions of Aryl Halides with Organostannanes" J.Chem.Soc.,Perkin Trans. 1. 2449-2450 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] 桧山爲次郎: "Copper (I) Salt Mediated 1,4-Reduction of d,B-Unsaturated Ketones Using Hydrosilanes" Chem.Commun. 22. 2159-2160 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] "応用化学講座4 有機合成化学" 朝倉書店, (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Masaki SHIMIZU: "Carbonyl-ene Approach to the Asymmetric Synthesis of 2-Keto-3-deoxy-D-gluconic Acid(KDG):A Combinatorial Sequence Using Sharpless Epoxidation" Synlett. (in press). (1997)

    • Related Report
      1996 Annual Research Report
  • [Publications] Emiko HAGIWARA: "NaOH-Promoted Cross-coupling Reactions of Organosilicon Compounds with Organic Halides:Practical Routes to Biaryls,Alkenylarenes and Conjugated Dienes" Tetrahedoun Lett.38. 439-442 (1997)

    • Related Report
      1996 Annual Research Report
  • [Publications] Hikaru SUGITA: "A Convenient Synthesis of Alkynylsilanes by Silylation of Copper(I)Alkynides" Chem.Lett.1996. 379-380 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Hikaru SUGITA: "A Novel Reduction of Zinc(II)Chloride with Samarium Metal and its Application to Silylation of l-Alkynes" Synlett. 1996. 637-639 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Hayao MATSUHASHI: "Synthesis of 5-Substituted Pyrimidine Nucleosides Through a Palladium-Catalyzed Cross-Coupling of Alkenylhalosilanes" Heterocycles. 42〔1〕. 375-384 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Kinichi GOUDA: "Cross-Coupling Reactions of Aryl Chlorides with Organochlorosilanes:Highly Effective Methods for Arylation or Alkenylation of Aryl Chlorides" J.Org.Chem.61〔21〕. 7232-7233 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] S.FURUTA: "Difluorination of 2-Substituted 1,1,1-Tris(methyltho)methanes by Oxidative Desulfurization-Fluorination.A New Route to Partially Fluorinated Olefins" Tetrahedron Lett.37. 7983-7986 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Tamejiro HIYAMA: "Chirality Transfer via the Palladium-catalyzed Cross-coupling Reaction of Optically Active 2-Cyclohexenylsilane:Stereochemical and Mechanistic Aspects" Organometallics. 15. 5762-5765 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Takeshi HATA: "Generation and Aldehyde Addition of a Zinc Carbenoid Substituted by Fluorine" Synlett. 1996. 831-832 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Satoru FURUTA: "Fluoro-Pummerer Rearrangement under Oxidatie Desulfurization Fluorination Conditions.facile Synthesis of Oligogfluoroalkyl Sulfides" Tetrahedron Lett.36. 8243-8246 (1995)

    • Related Report
      1996 Annual Research Report
  • [Publications] Yasuo HATANAKA: "Catalytic Asymmetric Hydrosilylation of Conjugated Dienes:Effective Control of Regio-and Enantioselectivities" Tetrahedron Lett.35. 7981-7982 (1994)

    • Related Report
      1995 Annual Research Report
  • [Publications] Manabu KUROBOSHI: "Halofluorination of Alkenes Using Dilute Hydrofluoric Acid" Bull.Chem.Soc.Jpn.68. 1799-1805 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Kiyoshi KANIE: "Synthesis and Properties of New Liquid Crystals Containing Trifluoromethylamino Group" Chem.Lett.67. 683-684 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Manabu KUROBOSHI: "Synthesis of Trifluoromethylamino-Substituted Pyridines and Pyrimidines by Oxidative Desulfurization-Fluorination" Tetrahedron Lett.36. 563-566 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Hayao MATSUHASHI: "Palladium-Catalyzed Cross-Coupling of Allylic Carbonates With Alkenylfluorosilanes in the Absence of Fluoride Ion" Tetrahedron Lett.36. 1539-1540 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Manabu KUROBOSHI: "Oxidative Desulfurization-Fluorination of 1-Substituted 2,2,2-Tris(methylthio)ethanol Inducrs Difluorination under Oxidation or Rearrangement" Tetrahedron Lett.36. 6121-6122 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Manabu KUROBOSHI: "Stereoselective Synthesis of(E)-ArCF=CFR and(E)-ArCH=CFR from ArCH(OH)CFBr2" Tetrahedron Lett.36. 6271-6274 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Hideaki OHMURA: "Catalytic Asymmetric Hydrosilylation of 1,3-Dienes with Difluoro(phenyl)silane" J.Organomet.Chem.499. 167-171 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Manabu KUROBOSHI: "Generation and Carbonyl Addition of Dibromofluoromethyllithium" Synlett. 987-988 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] 檜山 爲次郎: "フッ化水素を基盤とするフッ素化反応" 化学. 50. 66-67 (1995)

    • Related Report
      1995 Annual Research Report

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

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