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Reduction of nitriles to aldehydes
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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.