Reduction of nitriles to aldehydes
The combination of sodium hydride and zinc chloride enables a controlled reduction of nitriles to aldehydes via iminyl zinc intermediates. An in situ reaction of intermediates derived from aromatic nitriles with allylmetal nucleophiles affords homoallylamines. The method allows the reduction of aliphatic and aromatic nitriles under milder reaction conditions with wide functional group compatibility.
D. Y. Ong, S. Chiba, Synthesis, 2020, 52, 1369-1378.