Synthesis of Vinyl Trifluoromethyl Thioethers via Copper-Mediated Trifluoromethylthiolation of Vinyl Bromides

J Org Chem. 2015 Mar 6;80(5):2912-7. doi: 10.1021/acs.joc.5b00144. Epub 2015 Feb 24.

Abstract

A copper-mediated trifluoromethylthiolation of vinyl bromides has been developed. This method provides ready access to vinyl trifluoromethyl thioethers in good to high yields from simple, inexpensive starting materials. A broad substrate scope is achieved, and the reaction is compatible with various functional groups, including cyano, nitro, trifluoromethyl, alkoxy, amino, halide, and heterocyclic groups.

MeSH terms

  • Catalysis
  • Copper / chemistry*
  • Halogens / chemistry*
  • Heterocyclic Compounds / chemistry*
  • Hydrocarbons, Fluorinated / chemical synthesis*
  • Hydrocarbons, Fluorinated / chemistry
  • Nitriles / chemistry*
  • Sulfides / chemical synthesis*
  • Sulfides / chemistry
  • Vinyl Compounds / chemical synthesis*
  • Vinyl Compounds / chemistry

Substances

  • Halogens
  • Heterocyclic Compounds
  • Hydrocarbons, Fluorinated
  • Nitriles
  • Sulfides
  • Vinyl Compounds
  • Copper
  • vinyl bromide