3. Copper-Catalyzed Trifluoromethylation of Terminal Alkenes through Allylic C–H Bond Activation

Xu, J.; Fu, Y.;* Luo, D.-F.; Jiang, Y.-Y.; Xiao, B.; Liu, Z.-J.; Gong, T. J.; Liu, L.* J. Am. Chem. Soc. 2011, 133, 15300–15303. Download Link

Abstract: An unprecedented type of reaction for Cucatalyzed trifluoromethylation of terminal alkenes is reported. This reaction represents a rare instance of catalytic trifluoromethylation through C(sp3)
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.