Safe generation and use of bromine azide under continuous flow conditions – selective 1,2-bromoazidation of olefins

Abstract

Bromine azide (BrN₃), a useful but extremely toxic and explosive reagent for the preparation of vicinal 1,2-bromine azide compounds, was safely generated and reacted in situ with alkenes in a continuous flow photoreactor. BrN₃ was generated by a novel procedure from NaBr and NaN₃ in water, and efficiently extracted into an organic phase containing the alkene thus avoiding decomposition. The resulting addition products have been used for the preparation of several useful building blocks.