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

Journal of the American Chemical Society (2011-09-15)
Jun Xu, Yao Fu, Dong-Fen Luo, Yuan-Ye Jiang, Bin Xiao, Zhao-Jing Liu, Tian-Jun Gong, Lei Liu
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
5-(Trifluoromethyl)dibenzothiophenium trifluoromethanesulfonate, 97%
Sigma-Aldrich
5-(Trifluoromethyl)dibenzothiophenium tetrafluoroborate, 97%

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