Rhodium-Catalyzed Reductive Decyanation of Nitriles Using Hydrosilane as a Reducing Agent: Scope, Mechanism and Synthetic Application

Abstract

A rhodium-catalyzed reductive cleavage reaction of carbon-cyano bonds is developed using hydrosilane as a mild reducing agent. A wide range of nitriles, including aryl, benzyl, and <TEX>$\beta$</TEX>-hydrogen containing alkyl cyanides are applicable to this decyanation reaction. The method is also applicable to organic synthesis, in which benzyl cyanide is used as a benzyl anion equivalent and a cyano group functions as a removable ortho-directing group.