Photochemically Induced Radical Transformation of C(sp3)–H Bonds to C(sp3)–CN Bonds

A general protocol for direct transformation of unreactive C(sp3)–H bonds to C(sp3)–CN bonds has been developed. The C–H activation was effected by photoexcited benzophenone, and the generated carbon radical was subsequently trapped with tosyl cyanide to afford the corresponding nitrile in a highly efficient manner. The present methodology is widely applicable to versatile starting materials and, thus, serves as a powerful tool for selective one-carbon elongation for construction of architecturally complex molecules.