Polymer-Supported Carbene Complexes of Palladium: Well-Defined, Air-Stable, Recyclable Catalysts for the Heck Reaction

J. Schwarz, Volker P. W. Böhm, Michael G. Gardiner, M. Grosche, Wolfgang A. Herrmann, Wolfgang Hieringer, Gabriele Raudaschl‐Sieber

Chemistry - A European Journal · 2000 · 327 citations · 0 references

DOIFull text

Open access

Concepts

Abstract

N-Heterocyclic dicarbene chelate complexes of formula [cis-CH2N(H)C=C(H)N(R)C2PdX2] (X = Br, I; R = (CH2)nOH; n = 2, 3) have been prepared and structurally characterized (for X= I, n = 2). The complexes were immobilized on a functionalized polystyrene support (Wang resin) through one of the oxygen centres. The complexes efficiently catalyze the Heck reaction of activated and non-activated arylbromides, are recyclable under aerobic conditions and exhibit hardly any leaching, which is in line with our theoretical investigations on ligand dissociation energies related to Pd0 and PdII centres.