Switchable 2,2,2-Trifluoroethylation and gem-Difluorovinylation of Organoboronic Acids with 2,2,2-Trifluorodiazoethane

The transition-metal-free 2,2,2-trifluoroethylation and gem-difluorovinylation of arylboronic acids were developed. By employing different reaction conditions, these transformations provide both (2,2,2-trifluoroethyl)arenes and gem-difluorovinylarenes from arylboronic acids and 2,2,2-trifluorodiazoethane. The operation is simple and scalable with good functional group tolerance.