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Beilstein J Org Chem. 2013 Aug 16;9:1698-704. doi: 10.3762/bjoc.9.194. eCollection 2013.

Gallium-containing polymer brush film as efficient supported Lewis acid catalyst in a glass microreactor.

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  • 1Laboratory of Molecular Nanofabrication, MESA+ Institute for Nanotechnology, University of Twente, P.O. Box 217, 7500 AE Enschede, The Netherlands.

Abstract

Polystyrene sulfonate polymer brushes, grown on the interior of the microchannels in a microreactor, have been used for the anchoring of gallium as a Lewis acid catalyst. Initially, gallium-containing polymer brushes were grown on a flat silicon oxide surface and were characterized by FTIR, ellipsometry, and X-ray photoelectron spectroscopy (XPS). XPS revealed the presence of one gallium per 2-3 styrene sulfonate groups of the polymer brushes. The catalytic activity of the Lewis acid-functionalized brushes in a microreactor was demonstrated for the dehydration of oximes, using cinnamaldehyde oxime as a model substrate, and for the formation of oxazoles by ring closure of ortho-hydroxy oximes. The catalytic activity of the microreactor could be maintained by periodic reactivation by treatment with GaCl3.

KEYWORDS:

Lewis acid catalysis; dehydration of oximes; flow chemistry; gallium; microreactors; polymer brushes

PMID:
24062830
PMCID:
PMC3778416
DOI:
10.3762/bjoc.9.194
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