Copper(I)-Oxide-Mediated Cyanation of Arenediazonium Tetrafluoroborates with Trimethylsilyl Cyanide: A Method for Synthesizing Aromatic Nitriles

A Cu2O-mediated cross coupling of arenediazonium tetrafluoroborates with trimethylsilyl cyanide to form aromatic nitriles is presented. This protocol tolerates a wide range of functional groups and gives good to excellent yields under mild conditions. Cu2O provides appealing and convenient access to aromatic nitriles compared with the traditional Sandmeyer reaction with toxic CuCN via nucleophilic substitution under relatively harsh conditions.