Studies on Carbon-Carbon Bond Forming Reactions Utilizing Activation of Unsaturated Hydrocarbons and Heteroaromatic Compounds by Metal Sulfonate Catalysts

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  • Tsuchimoto Teruhisa
    Department of Applied Chemistry, School of Science and Technology, Meiji University

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  • 金属スルホナート触媒による不飽和炭化水素および複素芳香族化合物の活性化を利用した炭素‐炭素結合形成反応に関する研究
  • キンゾク スルホナート ショクバイ ニ ヨル フホウワ タンカスイソ オヨビ フクソ ホウコウゾク カゴウブツ ノ カッセイカ オ リヨウ シタ タンソ タンソ ケツゴウ ケイセイ ハンノウ ニ カンスル ケンキュウ

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Lewis acids have been used as a mediator or a catalyst so far mainly for activation of heteroatom-containing compounds like carbonyl compounds, imines and alkyl halides. In contrast, we have been focusing on developing new carbon-carbon bond forming reactions utilizing activation of hydrocarbons by a metal sulfonate catalyst. In this context, we found that arenes as well as heterocyclic arenes add to alkynes in the presence of indium triflate [In (OTf)3, Tf=SO2CF3] as a catalyst. These findings are followed by development of facile synthesis of aryl-and heteroarylannulated [a] carbazoles by the reaction of propargyl ethers with 2-aryl-and 2-heteroarylindoles. In addition to the above reactions, metal triflates catalyzed dimerization of vinylarenes with the aid of a palladium catalyst (activation of C = C), nucleophilic substitution using a pyrrolyl group as a carbon leaving group (activation of C-C) and oxidative coupling between lactams and heterocyclic arenes (activation of C-H).

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