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Insights into the catalytic activity of [Pd(NHC)(cin)Cl] (NHC=IPr, IPrCl, IPrBr) complexes in the Suzuki-Miyaura reaction

Frédéric Izquierdo, Caroline Zinser, Yury Minenkov, David B Cordes, Alexandra MZ Slawin, Luigi Cavallo, Fady Nahra (UGent) , Catherine Cazin (UGent) and Steven Nolan (UGent)
(2018) CHEMCATCHEM. 10(3). p.601-611
Author
Organization
Abstract
The influence of C-4,C-5-halogenation on palladium N-heterocyclic carbene complexes and their activity in the Suzuki-Miyaura reaction were investigated. Two [Pd(NHC)(cin)Cl] complexes bearing IPrCl and IPrBr ligands (IPr=1,3-bis(2,6-diisopropyl-phenyl)imidazol-2-ylidene; cin=cinnamyl) were synthesized. After determining the electronic and steric properties of these ligands, their properties were compared to those of [Pd(IPr) (cin)Cl]. The three palladium complexes were studied by using DFT calculations to delineate their behavior in the activation step leading to the putative 12-electron active catalyst. Experimentally, their catalytic activity in the Suzuki-Miyaura reaction involving a wide range of coupling partners (30 entries) at low catalyst loading was studied.
Keywords
density functional calculations, carbene ligands, cross-coupling, palladium, reaction mechanisms, N-HETEROCYCLIC CARBENE, CROSS-COUPLING REACTIONS, ORTHO-SUBSTITUTED BIARYLS, TRANSITION-METAL-COMPLEXES, ROOM-TEMPERATURE, ARYL CHLORIDES, ELECTRONIC-PROPERTIES, BUCHWALD-HARTWIG, ORGANOMETALLIC CHEMISTRY, SUPPORTED PRECATALYSTS

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Citation

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MLA
Izquierdo, Frédéric, et al. “Insights into the Catalytic Activity of [Pd(NHC)(Cin)Cl] (NHC=IPr, IPrCl, IPrBr) Complexes in the Suzuki-Miyaura Reaction.” CHEMCATCHEM, vol. 10, no. 3, 2018, pp. 601–11, doi:10.1002/cctc.201701279.
APA
Izquierdo, F., Zinser, C., Minenkov, Y., Cordes, D. B., Slawin, A. M., Cavallo, L., … Nolan, S. (2018). Insights into the catalytic activity of [Pd(NHC)(cin)Cl] (NHC=IPr, IPrCl, IPrBr) complexes in the Suzuki-Miyaura reaction. CHEMCATCHEM, 10(3), 601–611. https://doi.org/10.1002/cctc.201701279
Chicago author-date
Izquierdo, Frédéric, Caroline Zinser, Yury Minenkov, David B Cordes, Alexandra MZ Slawin, Luigi Cavallo, Fady Nahra, Catherine Cazin, and Steven Nolan. 2018. “Insights into the Catalytic Activity of [Pd(NHC)(Cin)Cl] (NHC=IPr, IPrCl, IPrBr) Complexes in the Suzuki-Miyaura Reaction.” CHEMCATCHEM 10 (3): 601–11. https://doi.org/10.1002/cctc.201701279.
Chicago author-date (all authors)
Izquierdo, Frédéric, Caroline Zinser, Yury Minenkov, David B Cordes, Alexandra MZ Slawin, Luigi Cavallo, Fady Nahra, Catherine Cazin, and Steven Nolan. 2018. “Insights into the Catalytic Activity of [Pd(NHC)(Cin)Cl] (NHC=IPr, IPrCl, IPrBr) Complexes in the Suzuki-Miyaura Reaction.” CHEMCATCHEM 10 (3): 601–611. doi:10.1002/cctc.201701279.
Vancouver
1.
Izquierdo F, Zinser C, Minenkov Y, Cordes DB, Slawin AM, Cavallo L, et al. Insights into the catalytic activity of [Pd(NHC)(cin)Cl] (NHC=IPr, IPrCl, IPrBr) complexes in the Suzuki-Miyaura reaction. CHEMCATCHEM. 2018;10(3):601–11.
IEEE
[1]
F. Izquierdo et al., “Insights into the catalytic activity of [Pd(NHC)(cin)Cl] (NHC=IPr, IPrCl, IPrBr) complexes in the Suzuki-Miyaura reaction,” CHEMCATCHEM, vol. 10, no. 3, pp. 601–611, 2018.
@article{8555583,
  abstract     = {{The influence of C-4,C-5-halogenation on palladium N-heterocyclic carbene complexes and their activity in the Suzuki-Miyaura reaction were investigated. Two [Pd(NHC)(cin)Cl] complexes bearing IPrCl and IPrBr ligands (IPr=1,3-bis(2,6-diisopropyl-phenyl)imidazol-2-ylidene; cin=cinnamyl) were synthesized. After determining the electronic and steric properties of these ligands, their properties were compared to those of [Pd(IPr) (cin)Cl]. The three palladium complexes were studied by using DFT calculations to delineate their behavior in the activation step leading to the putative 12-electron active catalyst. Experimentally, their catalytic activity in the Suzuki-Miyaura reaction involving a wide range of coupling partners (30 entries) at low catalyst loading was studied.}},
  author       = {{Izquierdo, Frédéric and Zinser, Caroline and Minenkov, Yury and Cordes, David B and Slawin, Alexandra MZ and Cavallo, Luigi and Nahra, Fady and Cazin, Catherine and Nolan, Steven}},
  issn         = {{1867-3880}},
  journal      = {{CHEMCATCHEM}},
  keywords     = {{density functional calculations,carbene ligands,cross-coupling,palladium,reaction mechanisms,N-HETEROCYCLIC CARBENE,CROSS-COUPLING REACTIONS,ORTHO-SUBSTITUTED BIARYLS,TRANSITION-METAL-COMPLEXES,ROOM-TEMPERATURE,ARYL CHLORIDES,ELECTRONIC-PROPERTIES,BUCHWALD-HARTWIG,ORGANOMETALLIC CHEMISTRY,SUPPORTED PRECATALYSTS}},
  language     = {{eng}},
  number       = {{3}},
  pages        = {{601--611}},
  title        = {{Insights into the catalytic activity of [Pd(NHC)(cin)Cl] (NHC=IPr, IPrCl, IPrBr) complexes in the Suzuki-Miyaura reaction}},
  url          = {{http://dx.doi.org/10.1002/cctc.201701279}},
  volume       = {{10}},
  year         = {{2018}},
}
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