Radical Hydroboration and Hydrosilylation of gem-Difluoroalkenes: Synthesis of α-Difluorinated Alkylborons and Alkylsilanes

A first example of radical hydroboration and hydrosilylation of gem-difluoroalkenes using ABIN as the radical initiator is described. This protocol features good functional group tolerance, operational simplicity, high atom economy, and easy scale-up, enabling efficient assembly of a wide range of alpha-difluorinated alkylborons and alkylsilanes in moderate to excellent yields. The synthetic utility of these products is demonstrated by further transformation of the C-B bond and C-Si bond into valuable CF2-containing molecules.