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

摘要

Aldehydes are converted into nitriles in a one-pot reaction by treatment with H_2NOHHCl in dipolar aprotic solvents under heating. Amongst various solvents NMP offers the best results. No competitive ether cleavae (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 for-mation. Excellent to moderate selecivity is observed during in-termolecular competition etween pair of aldehydes with varying electronic and steric requirements.