Copper-catalyzed trifluoromethylation of terminal alkenes through allylic C-H bond activation

J Am Chem Soc. 2011 Oct 5;133(39):15300-3. doi: 10.1021/ja206330m. Epub 2011 Sep 13.


An unprecedented type of reaction for Cu-catalyzed trifluoromethylation of terminal alkenes is reported. This reaction represents a rare instance of catalytic trifluoromethylation through C(sp(3))-H activation. It also provides a mechanistically unique example of Cu-catalyzed allylic C-H activation/functionalization. Both experimental and theoretical analyses indicate that the trifluoromethylation may occur via a Heck-like four-membered-ring transition state.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Carbon / chemistry*
  • Catalysis
  • Copper / chemistry*
  • Hydrogen / chemistry*
  • Methylation
  • Models, Molecular
  • Molecular Conformation


  • Alkenes
  • Carbon
  • Copper
  • Hydrogen