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

Give and take: Regioselective incorporation of a particular functional group into aliphatic sites by direct activation of unreactive C−H bonds remains challenging. Herein a new protocol for the regioselective vinylation of unactivated C(sp³)−H bonds is reported. The activation of a remote C(sp³)−H bond is promoted by a C‐centered radical instead of the commonly used N and O radicals.

Abstract

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(sp³)−H bonds by a hydrogen‐atom transfer process, the site‐selective vinylation of remote C(sp³)−H bonds still remains underexplored. Reported herein is a new protocol for the regioselective vinylation of unactivated C(sp³)−H bonds. The remote C(sp³)−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.

from A via a.sfakia on Inoreader http://bit.ly/2EVyK2r