Regioselective Vinylation of Remote Unactivated C(sp3)-H Bonds: Access to Complex Fluoroalkylated Alkenes

Regioselective incorporation of a particular functional group into aliphatic sites by direct activation of unreactive C-H bonds is of great synthetic value. Despite advances in radical-mediated functionalization of C(sp(3))-H bonds by a hydrogen-atom transfer process, the site-selective vinylation of remote C(sp(3))-H bonds still remains underexplored. Reported herein is a new protocol for the regioselective vinylation of unactivated C(sp(3))-H bonds. The remote C(sp(3))-H activation is promoted by a C-centered radical instead of the commonly used N and O radicals. The reaction possesses high product diversity and synthetic efficiency, furnishing a plethora of synthetically valuable E alkenes bearing tri-/di-/mono-fluoromethyl and perfluoroalkyl groups.