PolyHIPE supports in batch and flow-through suzuki cross-coupling reactions

Jane F. Brown, Peter Krajnc, Neil R. Cameron

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75 Citations (Scopus)

Abstract

As part of ongoing research efforts to discover alternative support materials to polymer beads for use in polymer-supported synthesis, particularly under flow-through conditions, this work involves the synthesis of PolyHIPE (High Internal Phase Emulsion) polymer monoliths. PolyHIPEs containing high loadings of chloromethyl groups were efficiently prepared by the direct copolymerization of 4-vinylbenzyl chloride and divinylbenzene monomers. The 'Merrifield' PolyHIPE proved to be an excellent support for batch and flow-through Suzuki cross-coupling reactions. A remarkably high yield of pure biaryl product was obtained using the PolyHIPE support in cubic form and utilizing an electron-rich boronic acid. In comparison to polymer beads, this material was found to be a much more efficient support in both batch and continuous flow modes. PolyHIPE converted a greater amount of chloromethyl groups into biaryl product under identical reaction conditions. It is suggested that the absence of channelling with PolyHIPE monoliths gives better performance under flow-through conditions than permanently porous beads.

Original languageEnglish
Pages (from-to)8565-8572
Number of pages8
JournalIndustrial & Engineering Chemistry Research
Volume44
Issue number23
DOIs
Publication statusPublished - 9 Nov 2005
Externally publishedYes

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