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J Am Chem Soc. 2004 Apr 28;126(16):5046-7. doi: 10.1021/ja049759r.

Structure and reactivity of "unusual" N-heterocyclic carbene (NHC) palladium complexes synthesized from imidazolium salts.

Journal of the American Chemical Society

Hélène Lebel, Marc K Janes, André B Charette, Steven P Nolan

Affiliations

  1. Département de chimie, Université de Montréal, Succursale Centre-ville, Montréal, Québec, Canada. [email protected]

PMID: 15099069 DOI: 10.1021/ja049759r

Abstract

The reaction between palladium acetate and IMES.HCl leads to the formation of a novel palladium complex. The X-ray crystal structure analysis reveals that the palladium is C(2) bound to one NHC ligand (the normal binding mode), whereas the second ligand is attached through the C(5) carbon of the second imidazolium. The metalation site on the imidazolium salt is strongly influenced by the presence of base. Furthermore, the binding mode of the NHC to Pd is shown to substantially affect the catalytic behavior of the palladium complexes in cross-coupling reactions.

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