New protocols for controlled reduction of carboxamides to either alcohols or amines were established using a combination of sodium hydride (NaH) and zinc halides (ZnX ). Use of a different halide on ZnX dictates the selectivity, wherein the NaH-ZnI system delivers alcohols and NaH-ZnCl gives amines. Extensive mechanistic studies by experimental and theoretical approaches imply that polymeric zinc hydride (ZnH ) is responsible for alcohol formation, whereas dimeric zinc chloride hydride (H-Zn-Cl) is the key species for the production of amines.
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