Silver-catalyzed Vinylic C–F Bond Activation: Synthesis of 2-Fluoroindoles from β,β-Difluoro-<i>o</i>-sulfonamidostyrenes

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  • Fujita Takeshi
    Division of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba
  • Watabe Yota
    Division of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba
  • Yamashita Shigeyuki
    Division of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba
  • Tanabe Hiroyuki
    Division of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba
  • Nojima Tomoya
    Division of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba
  • Ichikawa Junji
    Division of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba

Abstract

An electrophilic 5-endo-trig cyclization of β,β-difluoro-o-sulfonamidostyrenes was performed in 1,1,1,3,3,3-hexafluoropropan-2-ol using a Ag(I) catalyst and N,O-bis(trimethylsilyl)acetamide. In this process, vinylic C–F bond activation was achieved via silver-catalyzed β-fluorine elimination, accompanied by C–N bond formation, which led to the synthesis of 2-fluoroindoles.

Journal

  • Chemistry Letters

    Chemistry Letters 45 (8), 964-966, 2016

    The Chemical Society of Japan

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