Metal-free regioselective hydrobromination of alkynes through C[sbnd]H/C[sbnd]Br activation

Abstract

A metal-free regioselective hydrobromination of alkynes has been developed to provide the Markovnikov-type vinyl bromides in good yields using dibromomethane/N,N-dimethylaniline as in-situ ‘HBr’ source. This protocol also represents an elegant example of the activation of sp2 CH and CBr bonds in one pot, in which ‘HBr’ is generated and transferred under mild metal-free conditions. D-incorporated experiments were employed to investigate the reaction mechanism and a plausible reaction path was proposed.