Copper-Catalyzed Regioselective Cyanation of Indoles via C-H Bond Activation with α-Aminoacetonitriles

Abstract A metal-free and organic cyanating agent, 2-(diisopropylamino)acetonitrile is disclosed for the regioselective synthesis of cyanated indoles such as 2-cyanoindole and 3-cyanoindole derivatives. This method can tolerate a variety of functional groups and can furnish the corresponding cyanated products in moderate to high yields. Moreover, Cu/PhSiH3 system has been identified for the regioselective cleavage of C–H bonds of indoles by the use of metal-free CN sources via a one-pot sequential iodination/cyanation. This cost effective, homogeneous and metal-free CN source system represents the best reaction efficiency in these methodologies.