A new conversion of nitriles into acetyl compounds: Nickel-catalysed methylation by trimethylaluminium

Abstract

Nickel acetylacetonate catalyses the methylation of nitriles by trimethylaluminium. Methylation occurs in hydrocarbon solvent at near ambient temperature to give, upon hydrolysis, acetyl compounds (RCN → RCOMe). The following nitriles have been converted into acetyl compounds in moderate to good yields: benzonitrile, dodecyl cyanide, benzyl cyanide, diphenylacetonitrile, p-chlorobenzo-nitrile and glutaronitrile. Side reactions of the ketenimide formation-and- condensation type appear to occur less than with methyllithium and methyl Grignard reagents.