Journal of the American Chemical Society 2011-10-05

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

Jun Xu, Yao Fu, Dong-Fen Luo, Yuan-Ye Jiang, Bin Xiao, Zhao-Jing Liu, Tian-Jun Gong, Lei Liu

Index: J. Am. Chem. Soc. 39th ed., 133 , 15300-15303, (2011)

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Abstract

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.