Abstract: Sodium cyanohydridoborate (NaBH3CN) reduces a wide variety of organic functional groups with remarkable selectivity. The reduction of aldehydes and ketones is pH dependent, the reaction proceeding readily at pH 3-4. Oximes are smoothly reduced to alkylhydroxylamines and enamines are reduced to amines under acid catalysis. Reaction of an aldehyde or ketone with ammonia, primary amine, or secondary amine at pH-7 in the ...
