A simple and highly efficient one-pot chemoselective synthesis of nitriles from aldehydes: Mechanistic insight and selectivity control through modulation of electronic and steric factors

Abstract

Aldehydes are converted into nitriles in a one-pot reaction by treatment with H2NOH.HCl in dipolar aprotic solvents under heating. Amongst various solvents NMP offers the best results. No competitive ether cleavage (e.g. methoxy, benzyloxy) or aromatic nucleophilic substitution (e.g. nitro or chloro) takes place for substrates bearing such functionalities. Electronic and steric factors around the aldehyde carbon affect the rate of nitrile formation. Excellent to moderate selectivity is observed during intermolecular competition between pair of aldehydes with varying electronic and steric requirements.