Immobilized DMAP derivatives rivaling homogeneous DMAP

Abstract

The copper-catalyzed Huisgen reaction between azides and alkynes was utilized to covalently attach derivatives of 4-(dimethylamino)pyridine (DMAP) to a polystyrene resin (PS) support. The catalytic potential of these constructs as determined in acylation and aza-Morita-Baylis-Hillman reactions far exceeds that of commercially available DMAP-PS resins and is fully competitive with DMAP in homogeneous solution. Immobilization of 3,4-diaminopyridine catalysts on polystyrene by using the copper-catalyzed Huisgen reaction allowed the preparation of new supported catalysts ofunprecedented catalytic activity in acylation and aza-Morita-Baylis-Hillman reactions. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.