Tris(pentafluorophenyl)borane-Catalyzed Stereospecific Bromocyanation of Styrene Derivatives with Cyanogen Bromide

We, herein, report on the bromocyanation of styrene derivatives with cyanogen bromide in the presence of tris(pentafluorophenyl)borane which functions as a Lewis acid catalyst that can effectively activate cyanogen bromide. This reaction proceeds through a stereospecific syn-addition. The protocol is operationally simple and provides practical access to β-bromonitriles.