Sequential bromination reactions from beads with methyltriphenylphosphonium tribromide groups

A reusable bromination reagent based on polystyrene beads with covalently appended methyltriphenylphosphonium tribromide groups has been developed. The results from bromination reactions of several structurally diverse unsaturated substrates with the beads and with solutions of a non-polymeric model brominating reagent, methyltriphenylphosphonium tribromide, are described. It is shown that the reactions are highly regio- and stereo-selective and can be conducted easily. Copyright (C) 2010 John Wiley & Sons, Ltd.