The Reductive Decyanation of Nitriles by Alkali Fusion

Abstract The use of the nitrile functional group for the activation of an α-carbon for deprotonation and alkylation is an important reaction in organic synthesis.2 However, a problem often encountered is the removal of the nitrile group after its activating properties have been exploited. Reported methods include dehydrocyanation,3 oxidative decyanation,4 and, more commonly, reductive decyanation. The reductive decyanation of nitriles, as depicted in Scheme 1, has been reported employing metal hydrides,5 transition metal complexes,6 electrolysis7 and alkali metals in a variety of solvents.8 All of these methods, however, suffer shortcomings such as expense, use of hazardous reagents, and competing side-reactions (e.g.