A new protocol for the controlled reduction of nitriles to aldehydes was developed
using a combination of sodium hydride and zinc chloride. The iminyl zinc intermediates
derived from aromatic nitriles could be further functionalized with allylmetal nucleophiles
to afford homoallylamines. As the method allows the reduction of various aliphatic
and aromatic nitriles with a concise procedure under milder reaction conditions and
exhibits wide functional group compatibility, it is well suited for use in various
opportunities in chemical synthesis.
Key words
nitriles - aldehydes - sodium hydride - zinc chloride - reduction