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Issue 3, 2016
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Safe generation and use of bromine azide under continuous flow conditions – selective 1,2-bromoazidation of olefins

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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.

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

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Supplementary files

Article information


Submitted
25 Nov 2015
Accepted
02 Dec 2015
First published
02 Dec 2015

This article is Open Access

Org. Biomol. Chem., 2016,14, 853-857
Article type
Communication
Author version available

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

D. Cantillo, B. Gutmann and C. Oliver Kappe, Org. Biomol. Chem., 2016, 14, 853
DOI: 10.1039/C5OB02425K

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