Mimicking the vanadium bromoperoxidases reactions: Mild and selective bromination of arenes and alkenes in a two-phase system

Article abstract of DOI:10.1016/0040-4039(94)85333-9

Vanadium bromoperoxidases catalyze the oxidation of bromide ion by hydrogen peroxide to a bromine-equivalent intermediate. This, in turn, brominates organic molecules. The hypothesis is made that the former reaction takes place in the hydrophilic portion of the enzyme whereas the latter proceeds in a hydrophobic one in which the brominating intermediate is rapidly transferred. We have reproduced such situation by employing a two-phase (H₂O/CHCl₃) system. In the aqueous acid phase H₂O₂ and catalytic amounts of NH₄VO₃ are present, together with KBr. The substrates, i.e. aromatic hydrocarbons and alkenes are dissolved in CHCl₃. The bromination proceeds smoothly with stirring, at 25°C, providing high yields of the corresponding brominated products.