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Mixed phosphite/N-heterocyclic carbene complexes : synthesis, characterization and catalytic studies

(2010) ORGANOMETALLICS. 29(6). p.1443-1450
Author
Organization
Abstract
A series of mixed P(OR)(3)/NHC Pd complexes was synthesized and fully characterized. The steric properties of both types of ligands were computationally determined using X-ray data. These structural studies clearly show that N-heterocyclic carbenes modulate their bulkiness with respect to the steric requirements of the coligands. Catalytic studies were performed using this new class of complexes for the Suzuki-Miyaura reaction. It was found that alkoxide or hydroxide bases and/or alcohols were necessary to achieve good catalytic activity. Mechanistic studies were undertaken in order to gain insights into the role of alkoxide groups. These studies suggest that alcohols or alkoxide groups play a major role in the activation of the precatalyst to generate the catalytically active species. Catalytic studies proved these systems to be efficient using 0.1 mol % of Pd loading for the coupling of aryl, benzyl, and heterocyclic chlorides with boronic acids.
Keywords
CROSS-COUPLING REACTIONS, TEMPERATURE SUZUKI-MIYAURA, HINDERED ARYL CHLORIDES, ROOM-TEMPERATURE, TRIARYLPHOSPHITE COMPLEXES, PALLADIUM CATALYSTS, BUCHWALD-HARTWIG, NHC, LIGANDS, ELECTROPHILES

Citation

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MLA
Diebolt, Olivier, et al. “Mixed Phosphite/N-Heterocyclic Carbene Complexes : Synthesis, Characterization and Catalytic Studies.” ORGANOMETALLICS, vol. 29, no. 6, 2010, pp. 1443–50.
APA
Diebolt, O., Jurcik, V., da Costa, R. C., Braunstein, P., Cavallo, L., Nolan, S., … Cazin, C. (2010). Mixed phosphite/N-heterocyclic carbene complexes : synthesis, characterization and catalytic studies. ORGANOMETALLICS, 29(6), 1443–1450.
Chicago author-date
Diebolt, Olivier, Vaclav Jurcik, Rosenildo Correa da Costa, Pierre Braunstein, Luigi Cavallo, Steven Nolan, Alexandra MZ Slawin, and Catherine Cazin. 2010. “Mixed Phosphite/N-Heterocyclic Carbene Complexes : Synthesis, Characterization and Catalytic Studies.” ORGANOMETALLICS 29 (6): 1443–50.
Chicago author-date (all authors)
Diebolt, Olivier, Vaclav Jurcik, Rosenildo Correa da Costa, Pierre Braunstein, Luigi Cavallo, Steven Nolan, Alexandra MZ Slawin, and Catherine Cazin. 2010. “Mixed Phosphite/N-Heterocyclic Carbene Complexes : Synthesis, Characterization and Catalytic Studies.” ORGANOMETALLICS 29 (6): 1443–1450.
Vancouver
1.
Diebolt O, Jurcik V, da Costa RC, Braunstein P, Cavallo L, Nolan S, et al. Mixed phosphite/N-heterocyclic carbene complexes : synthesis, characterization and catalytic studies. ORGANOMETALLICS. 2010;29(6):1443–50.
IEEE
[1]
O. Diebolt et al., “Mixed phosphite/N-heterocyclic carbene complexes : synthesis, characterization and catalytic studies,” ORGANOMETALLICS, vol. 29, no. 6, pp. 1443–1450, 2010.
@article{8169274,
  abstract     = {A series of mixed P(OR)(3)/NHC Pd complexes was synthesized and fully characterized. The steric properties of both types of ligands were computationally determined using X-ray data. These structural studies clearly show that N-heterocyclic carbenes modulate their bulkiness with respect to the steric requirements of the coligands. Catalytic studies were performed using this new class of complexes for the Suzuki-Miyaura reaction. It was found that alkoxide or hydroxide bases and/or alcohols were necessary to achieve good catalytic activity. Mechanistic studies were undertaken in order to gain insights into the role of alkoxide groups. These studies suggest that alcohols or alkoxide groups play a major role in the activation of the precatalyst to generate the catalytically active species. Catalytic studies proved these systems to be efficient using 0.1 mol % of Pd loading for the coupling of aryl, benzyl, and heterocyclic chlorides with boronic acids.},
  author       = {Diebolt, Olivier and Jurcik, Vaclav and da Costa, Rosenildo Correa and Braunstein, Pierre and Cavallo, Luigi and Nolan, Steven and Slawin, Alexandra MZ and Cazin, Catherine},
  issn         = {0276-7333},
  journal      = {ORGANOMETALLICS},
  keywords     = {CROSS-COUPLING REACTIONS,TEMPERATURE SUZUKI-MIYAURA,HINDERED ARYL CHLORIDES,ROOM-TEMPERATURE,TRIARYLPHOSPHITE COMPLEXES,PALLADIUM CATALYSTS,BUCHWALD-HARTWIG,NHC,LIGANDS,ELECTROPHILES},
  language     = {eng},
  number       = {6},
  pages        = {1443--1450},
  title        = {Mixed phosphite/N-heterocyclic carbene complexes : synthesis, characterization and catalytic studies},
  url          = {http://dx.doi.org/10.1021/om9011196},
  volume       = {29},
  year         = {2010},
}

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