REDUCTION OF AZIDES WITH ZINC BOROHYDRIDE

Zinc borohydride in 1,2-dimethoxyethane provides an efficient procedure for the reduction of organic azides. Aroyl, acyl, and arylsulfonyl azides readily undergo reduction at room temperature to produce amides and sulfonamides in excellent yields; however, substitution with electron-withdrawing groups in the aroyl azides leads to the corresponding benzyl alcohols. Reduction of aryl and alkyl azides has also been achieved in high yields, under some modified conditions.