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Dibromination of alkenes with LiBr and H2O2 under mild conditions

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Abstract

Electron-rich and electron-poor alkenes, and alkenes bearing protecting groups can be efficiently and stereoselectively converted to trans-dibromides using LiBr/H2O2 and AcOH as a proton source in 1,4-dioxane. For most substrates addition of 0.1 mol% of PhTeTePh enhances the reaction rate and the yield of the products. Experimental data suggest that the brominating agent prepared in situ is molecular bromine and that LiBr assists the activation of H2O2 allowing bromination to occur using AcOH as a mild proton source in uncatalyzed experiments. Scale-up is feasible: 10.0 mmol of 1-octene was quantitatively converted to 1,2-dibromooctene in one hour of reaction at room temperature.

Graphical abstract: Dibromination of alkenes with LiBr and H2O2 under mild conditions

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Publication details

The article was received on 06 Nov 2017, accepted on 17 Nov 2017 and first published on 20 Nov 2017


Article type: Paper
DOI: 10.1039/C7NJ04300G
Citation: New J. Chem., 2018, Advance Article
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    Dibromination of alkenes with LiBr and H2O2 under mild conditions

    N. S. Martins and E. E. Alberto, New J. Chem., 2018, Advance Article , DOI: 10.1039/C7NJ04300G

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