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

doi:10.1039/c2dt32858e

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 journal › Article › peer-review

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 language	English
Pages (from-to)	7345-7353
Number of pages	9
Journal	Dalton Transactions
Volume	42
Early online date	7 Jan 2013
DOIs	https://doi.org/10.1039/c2dt32858e
Publication status	Published - 2013

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10.1039/c2dt32858e

Synergistic Ligand Effects in Palladium: Synergistic Ligand Effects in Palladium Catalysis
Cazin, C. S. J. (PI)
EPSRC
13/11/09 → 12/11/10
Project: Standard

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@article{677fc8f8021b433eacb3a10493792537,

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

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{\textquoteright}-bis-(2,6-diisopropylphenyl)imidazol-2-ylidene; XPhos = 2-dicyclohexylphosphino-2{\textquoteright},4{\textquoteright},6{\textquoteright}-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%.",

author = "Thibault Schmid and Jones, {Dale C.} and Olivier Diebolt and Furst, {Marc Robert Laurent} and Slawin, {Alexandra Martha Zoya} and Cazin, {Catherine S.J.}",

note = "The authors thank the Royal Society (University Research Fellowship to CSJC) for financial support. The authors are grateful to Umicore AG for generous gifts of palladium complexes and to the EPSRC National Mass Spectrometry Service Centre HRMS analysis.",

year = "2013",

doi = "10.1039/c2dt32858e",

language = "English",

volume = "42",

pages = "7345--7353",

journal = "Dalton Transactions",

issn = "1477-9226",

publisher = "ROYAL SOC CHEMISTRY",

}

TY - JOUR

T1 - Mixed phosphine/N-heterocyclic carbene palladium complexes

T2 - synthesis, characterization and catalytic use in aqueous Suzuki–Miyaura reactions

AU - Schmid, Thibault

AU - Jones, Dale C.

AU - Diebolt, Olivier

AU - Furst, Marc Robert Laurent

AU - Slawin, Alexandra Martha Zoya

AU - Cazin, Catherine S.J.

N1 - The authors thank the Royal Society (University Research Fellowship to CSJC) for financial support. The authors are grateful to Umicore AG for generous gifts of palladium complexes and to the EPSRC National Mass Spectrometry Service Centre HRMS analysis.

PY - 2013

Y1 - 2013

N2 - 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%.

AB - 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%.

U2 - 10.1039/c2dt32858e

DO - 10.1039/c2dt32858e

M3 - Article

SN - 1477-9226

VL - 42

SP - 7345

EP - 7353

JO - Dalton Transactions

JF - Dalton Transactions

ER -

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

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Synergistic Ligand Effects in Palladium: Synergistic Ligand Effects in Palladium Catalysis

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