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Issue 1, 2009
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Selective aerobic oxidative dibromination of alkenes with aqueous HBr and sodium nitrite as a catalyst

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Abstract

Various alkenes (internal, terminal, aryl and alkyl substituted) and 1,2-diphenylethyne were efficiently and selectively dibrominated using 2 equivalents of 48% aqueous hydrobromic acid, with air as an oxidant and sodium nitrite as a catalyst. Despite the presence of water, only trans dibromination occurred producing anti-1,2-dibromoalkanes and (E)-1,2-dibromo-1,2-diphenylethene. A comparison of resource demand, waste production and environmental, health and safety issues of the NaNO2 catalyzed aerobic bromination with molecular bromine and other oxidative bromination methods revealed that the proposed method is not only selective and effective but has a better environmental profile.

Graphical abstract: Selective aerobic oxidative dibromination of alkenes with aqueous HBr and sodium nitrite as a catalyst

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Publication details

The article was received on 28 Aug 2008, accepted on 15 Oct 2008 and first published on 17 Nov 2008


Article type: Paper
DOI: 10.1039/B814989E
Citation: Green Chem., 2009,11, 120-126
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    Selective aerobic oxidative dibromination of alkenes with aqueous HBr and sodium nitrite as a catalyst

    A. Podgoršek, M. Eissen, J. Fleckenstein, S. Stavber, M. Zupan and J. Iskra, Green Chem., 2009, 11, 120
    DOI: 10.1039/B814989E

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