A new strategy to construct a C=C-CF3 subunit via CuBr-catalyzed domino reaction of homopropargyl amines: an efficient synthesis of trifluoromethyl containing building blocks 4-trifluoromethyl-2,3-dihydro-pyrroliums

Chem Commun (Camb). 2014 Mar 21;50(23):3048-51. doi: 10.1039/c3cc49059a.

Abstract

A new strategy for the construction of a C=C-CF3 subunit has been developed via CuBr-catalyzed domino cyclization-trifluoromethylation of homopropargyl amines with Umemoto's reagent. 4-Trifluoromethyl-2,3-dihydro-pyrroliums were produced in high yields. The usefulness of these products has been demonstrated by the transformation of them into various other trifluoromethylated molecules.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemical synthesis
  • Amines / chemistry*
  • Bromides / chemistry
  • Catalysis
  • Copper / chemistry
  • Cyclization
  • Halogenation
  • Methylation
  • Pyrroles / chemical synthesis*
  • Pyrroles / chemistry

Substances

  • Amines
  • Bromides
  • Pyrroles
  • cupric bromide
  • Copper