Lithium/DTBB-Induced Reduction of N-Alkoxyamides and Acyl Azides

Abstract

A series of N-alkoxyamides and N-methoxy-N-methylamides (Weinreb amides) have been subjected to dealkoxylation by reductive cleavage of the N-O bond with lithium powder and a catalytic amount of DTBB (10 mol%) at room temperature, leading to the corresponding amides. When the reaction is performed under reflux conditions, the corresponding alkanes, resulting from a formal deaminocarbonylation process, are obtained. This methodology applied to acyl azides furnished the corresponding primary amides.

Key words

N-alkoxyamides - acyl azides - reduction - Li/DTBB (cat.) - amides - alkanes

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CAUTION: Acyl azides are potentially explosive when evaporated to dryness.