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 language | English |
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Pages (from-to) | 8565-8572 |
Number of pages | 8 |
Journal | Industrial & Engineering Chemistry Research |
Volume | 44 |
Issue number | 23 |
DOIs | |
Publication status | Published - 9 Nov 2005 |
Externally published | Yes |