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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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Publication details

The article was received on 25 Nov 2015, accepted on 02 Dec 2015 and first published on 02 Dec 2015


Article type: Communication
DOI: 10.1039/C5OB02425K
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Citation: Org. Biomol. Chem., 2016,14, 853-857
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    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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