Dichloroborane-dimethyl sulfide, a highly selective reducing agent for reduction of organyl azides to amines

Abstract

Dichloroborane-dimethyl sulfide reduces a variety of organyl azides, such as primary, secondary, tertiary, and aromatic to the corresponding amines in excellent yields. Cycloalkyl and benzylic azides are also readily reduced by this reagent. The reduction of azide with BHCl2 SMe2 is highly selective and many functional groups, such as halogen, ester, nitrile, aliphatic and aromatic nitro, survive in this process.