Comparative experimental and EXAFS studies in the Mizoroki-Heck reaction with heteroatom-functionalised N-heterocyclic carbene palladium catalysts


Fiddy, S.G., Evans, J., Neisius, T., Newton, M.A., Tsoureas, N., Tulloch, A.A.D. and Danopoulos, A.A. (2007) Comparative experimental and EXAFS studies in the Mizoroki-Heck reaction with heteroatom-functionalised N-heterocyclic carbene palladium catalysts. Chemistry-a European Journal, 13, (13), 3652-3659. (doi:10.1002/chem.200601278).

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Original Publication URL: http://dx.doi.org/10.1002/chem.200601278

Description/Abstract

A study on the Mizoroki-Heck coupling of selected aryl bromides with acrylates catalysed by a series of Pd complexes of bidentate pyridyl-, picolyl-, diphenylphosphinoethyl- and diphenylphosphinomethyl-functionalised N-heterocyclic carbene (NHC) is reported. The observed activity is dependent on the type of solvent and base used and the nature of the classical donors of the mixed-donor bidentate ligand and its bite angle. A mechanistic model is presented for the pyridine-functionalised NHC complexes based on an in situ EXAFS study under dilute catalyst conditions (2 mM Pd). The model involves pre-dissociation of the pyridine functionality and oxidative addition of ArBr in the early stages of the reaction, as well as formation of monomeric and dimeric Pd species at the time of substrate conversion.

Item Type: Article
ISSNs: 0947-6539 (print)
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Keywords: complexes, heck reaction, coupling reactions, exafs spectroscopy, curved-wave theory,carbene ligands, c-c, , efficient catalysts, catalysis, homogeneous, cyclopalladated compounds, palladium
Subjects: Q Science
Q Science > QD Chemistry
Divisions: University Structure - Pre August 2011 > School of Chemistry
ePrint ID: 54294
Date Deposited: 31 Jul 2008
Last Modified: 27 Mar 2014 18:37
URI: http://eprints.soton.ac.uk/id/eprint/54294

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