An efficient methodology to oxidize benzylic and cinnamyl alcohols to their corresponding nitriles in excellent yields has been developed. This methodology employs DDQ as an oxidant and TMSN(3) as a source of nitrogen in the presence of a catalytic amount of Cu(ClO(4))(2)·6H(2)O.

A Novel Oxidative Transformation of Alcohols to Nitriles: An Efficient Utility of Azides as a Nitrogen Source. -The title method tolerates a variety of oxidizable functional groups and a few useful protecting groups. -(ROKADE, B. V.; MALEKAR, S. K.; PRABHU*, K. R.; Chem. Commun. (Cambridge) 48 (2012) 44, 5506-5508, http://dx.