Copper-Catalyzed Oxidative Coupling of AIBN and Ketone-Derived Enoxysilanes to γ-Ketonitriles

A new and efficient oxidative coupling reaction between enoxysilane and alkylnitrile radicals derived from readily available AIBN and its analogues has been developed by using redox-active metal as a catalyst in which the redox-active copper is used for enhancing the electrophilicity of a free radical via coordination and bringing the radical and nucleophilic enol ether closer to facilitate the single-electron transfer. The present catalytic protocol afforded a variety of γ-ketonitriles in good to excellent yields with good functional group tolerance.