Reduction of Azides with Zinc Borohydride

Article abstract of DOI:10.1021/jo00094a021

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 temperatue 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.