Perfluoroalkyl-Chalcogenation of Alkynes

  • Yasufumi Ueda
    Department of Applied Chemistry, Faculty of Engineering, Okayama UniversityTsushima, Okayama 700
  • Masatomi Kanai
    Department of Applied Chemistry, Faculty of Engineering, Okayama UniversityTsushima, Okayama 700
  • Kenji Uneyama
    Department of Applied Chemistry, Faculty of Engineering, Okayama UniversityTsushima, Okayama 700

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<jats:title>Abstract</jats:title> <jats:p>Perfluoroalkyl-telluration of alkynes has been performed by a (PhTe)2–NaBH4–RfX system at a low temperature (−40, −80, or −100 °C) to give 2-(perfluoroalkyl)vinyl tellurides. Meanwhile, perfluoroalkyl-sulfenylation and perfluoroalkyl-selenation were less effective. The perfluoroalkyl-telluration proceeds mainly via both SRN1 process and photochemical addition of the in situ formed perfluoroalkyl phenyl telluride (RfTePh). The efficiency of the chalcogenolate anions for perfluoroalkyl-chalcogenation was found to be the order of PhS− &lt; PhSe− &lt; PhTe−.</jats:p>

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