Indirect monoalkylation of primary and secondary amines by reductive decyanation of α-aminonitriles with sodium cyanoborohydride-mercury bis(trifluoroacetate)

Article abstract of DOI:10.1016/0040-4020(96)00631-X

Secondary and tertiary amines are prepared from α-aminonitriles by selective reductive cleavage of the cyanide moiety. The α-aminonitriles in this case, function as 'masked' imine or iminium ions and are 'unmasked' by mercury(II) in the presence of sodium cyanoborohydride to obtain the reduced product. Secondary amines may be prepared indirectly from primary amines in good yield without danger of over alkylation.