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

(2013) DALTON TRANSACTIONS. 42(20). p.7345-7353
Author
Organization
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 co-ligand. 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%.
Keywords
CROSS-COUPLING REACTIONS, HIGHLY EFFICIENT, ARYL CHLORIDES, ROOM-TEMPERATURE, STRUCTURAL-CHARACTERIZATION, WATER, NHC, LIGANDS, HALIDES, SONOGASHIRA

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MLA
Schmid, Thibault E., et al. “Mixed Phosphine/N-Heterocyclic Carbene Palladium Complexes : Synthesis, Characterization and Catalytic Use in Aqueous Suzuki-Miyaura Reactions.” DALTON TRANSACTIONS, vol. 42, no. 20, 2013, pp. 7345–53.
APA
Schmid, T. E., Jones, D. C., Songis, O., Diebolt, O., Furst, M. R., Slawin, A. M., & Cazin, C. (2013). Mixed phosphine/N-heterocyclic carbene palladium complexes : synthesis, characterization and catalytic use in aqueous Suzuki-Miyaura reactions. DALTON TRANSACTIONS, 42(20), 7345–7353.
Chicago author-date
Schmid, Thibault E, Dale C Jones, Olivier Songis, Olivier Diebolt, Marc RL Furst, Alexandra MZ Slawin, and Catherine Cazin. 2013. “Mixed Phosphine/N-Heterocyclic Carbene Palladium Complexes : Synthesis, Characterization and Catalytic Use in Aqueous Suzuki-Miyaura Reactions.” DALTON TRANSACTIONS 42 (20): 7345–53.
Chicago author-date (all authors)
Schmid, Thibault E, Dale C Jones, Olivier Songis, Olivier Diebolt, Marc RL Furst, Alexandra MZ Slawin, and Catherine Cazin. 2013. “Mixed Phosphine/N-Heterocyclic Carbene Palladium Complexes : Synthesis, Characterization and Catalytic Use in Aqueous Suzuki-Miyaura Reactions.” DALTON TRANSACTIONS 42 (20): 7345–7353.
Vancouver
1.
Schmid TE, Jones DC, Songis O, Diebolt O, Furst MR, Slawin AM, et al. Mixed phosphine/N-heterocyclic carbene palladium complexes : synthesis, characterization and catalytic use in aqueous Suzuki-Miyaura reactions. DALTON TRANSACTIONS. 2013;42(20):7345–53.
IEEE
[1]
T. E. Schmid et al., “Mixed phosphine/N-heterocyclic carbene palladium complexes : synthesis, characterization and catalytic use in aqueous Suzuki-Miyaura reactions,” DALTON TRANSACTIONS, vol. 42, no. 20, pp. 7345–7353, 2013.
@article{8536944,
  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 co-ligand. 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%.},
  author       = {Schmid, Thibault E and Jones, Dale C and Songis, Olivier and Diebolt, Olivier and Furst, Marc RL and Slawin, Alexandra MZ and Cazin, Catherine},
  issn         = {1477-9226},
  journal      = {DALTON TRANSACTIONS},
  keywords     = {CROSS-COUPLING REACTIONS,HIGHLY EFFICIENT,ARYL CHLORIDES,ROOM-TEMPERATURE,STRUCTURAL-CHARACTERIZATION,WATER,NHC,LIGANDS,HALIDES,SONOGASHIRA},
  language     = {eng},
  number       = {20},
  pages        = {7345--7353},
  title        = {Mixed phosphine/N-heterocyclic carbene palladium complexes : synthesis, characterization and catalytic use in aqueous Suzuki-Miyaura reactions},
  url          = {http://dx.doi.org/10.1039/c2dt32858e},
  volume       = {42},
  year         = {2013},
}

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