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

Jane F. Brown (Author), Peter Krajnc (Author), Neil R. Cameron (Author)

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.

Keywords

polimerni nosilci;monolitni polimeri;emulzijska polimerizacija;sinteza na trdni fazi;sintezne reakcije tipa Suzuki;polymer supports;polymer monoliths;emulsion polymerisation;solid-phase synthesis;cross-coupling reactions;

Data

Language:	English
Year of publishing:	2005
Typology:	1.01 - Original Scientific Article
Organization:	UM FKKT - Faculty of Chemistry and Chemical Engineering
UDC:	547:678
COBISS:	9473558
ISSN:	0888-5885
Views:	1714
Downloads:	83
Average score:	0 (0 votes)
Metadata:

Other data

Secondary language:	English
Secondary keywords:	polimerni nosilci;monolitni polimeri;emulzijska polimerizacija;sinteza na trdni fazi;sintezne reakcije tipa Suzuki;
URN:	URN:SI:UM:
Pages:	str. 8565-8572
Volume:	44
Issue:	23
Chronology:	2005
ID:	8718283