Metal-Free Cyanation of gem-Difluoroalkenes via Azide-Mediated C–C Double Bond Fragmentation

Abstract

Activation and cleavage of C−C double bonds are long-standing challenges in synthetic chemistry. Herein, we report an unprecedented azide-mediated C−C double bond fragmentation of gem-difluoroalkenes under mild and metal-free conditions, enabling the efficient synthesis of structurally diverse aromatic nitriles in moderate to good yields. This protocol is also amenable to the cyanation of gem-dichloro and dibromo alkenes. This reaction features simple operation and good functional group compatibility and can be implemented at a gram scale.