Mixed phosphine/N-heterocyclic carbene palladium complexes: synthesis, characterization and catalytic use in aqueous Suzuki–Miyaura reactions

Thibault Schmid, Dale C. Jones, Olivier Diebolt, Marc Robert Laurent Furst, Alexandra Martha Zoya Slawin, Catherine S.J. Cazin

Research output: Contribution to journalArticlepeer-review

74 Citations (Scopus)

Abstract

A series of N-heterocyclic carbene (NHC)/PR3 palladium(II) and palladium(0) complexes has been synthesized and fully characterized. X-ray crystallographic data have allowed comparison of ligand steric properties. The NHC ligand was found to vary its steric properties as a function of the phosphine coligand. These complexes display interesting catalytic properties in the Suzuki–Miyaura reaction performed in aqueous media. The pre-catalyst [PdCl2(IPr)(XPhos)] (IPr = N,N’-bis-(2,6-diisopropylphenyl)imidazol-2-ylidene; XPhos = 2-dicyclohexylphosphino-2’,4’,6’-triisopropylbiphenyl) was found to be the most efficient system, promoting the coupling of a wide range of aryl chlorides with boronic acids in aqueous media with a typical catalyst loading of 0.03 mol%.
Original languageEnglish
Pages (from-to)7345-7353
Number of pages9
JournalDalton Transactions
Volume42
Early online date7 Jan 2013
DOIs
Publication statusPublished - 2013

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