Lewis Acid Promoted Single C–F Bond Activation of the CF₃ Group: S_N1′‐Type 3,3‐Difluoroallylation of Arenes with 2‐Trifluoromethyl‐1‐alkenes

Abstract

Abstract Activation of the sp 3 C−F bond in 2‐trifluoromethyl‐1‐alkenes was accomplished through treatment with a Lewis acid. In the presence of an equimolar amount of EtAlCl 2 , the (trifluoromethyl)alkenes readily underwent an S N 1′‐type reaction with arenes through a Friedel–Crafts‐type mechanism via elimination of a fluoride ion to afford 3,3‐difluoroallylated arenes in good yields. This selective activation of one C−F bond of the CF 3 group provides a synthetic method for accessing biologically and synthetically important 1,1‐difluoro‐1‐alkenes.