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.