Zinc-Modified Cyanoborohydride as a Selective Reducing Agent

Article abstract of DOI:10.1021/jo00211a028

Zinc-modified cyanoborohydride generated from sodium cyanoborohydride and zinc chloride in a 2:1 molar ratio is found to be a selective and versatile reducing agent.The reagent in diethyl ether reduces aldehydes, ketones and acid chlorides to the corresponding alcohols but does not reduce acid anhydrides, acids, esters and tertiary amides.The reagent in methanol is very useful for reduction of enamines, reductive amination of aldehydes and ketones, reductive methylation of amines, and deoxygenation of aldehydes and ketones.