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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
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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 10.3 (2018): 601–611. Print.
APA
Izquierdo, F., Zinser, C., Minenkov, Y., Cordes, D. B., Slawin, A. M., Cavallo, L., Nahra, F., et al. (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.
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): 601–611.
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.
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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