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Influence of a very bulky N-heterocyclic carbene in gold-mediated catalysis

(2011) ORGANOMETALLICS. 30(20). p.5463-5470
Author
Organization
Abstract
The syntheses of the free carbene IPr* (IPr* = 1,3-bis (2,6-b is (diphenylmethyl)-4-methylphenyl)imidazol-2-ylidene) and related gold complexes [Au(IPr*)Cl] (C1) and [Au(IPr*)(NTf2)] (C2) were achieved in high yields. The % V-Bur of IPr* for both gold complexes was measured, revealing IPr* as one of the bulkiest NHCs on gold complexes reported to date. In addition, the catalytic activity of C1 and C2 in several reactions, typically catalyzed by Au-I complexes, was investigated. Examples include the tandem alkoxylation/lactonization of gamma-hydroxy-alpha,beta-acetylenic esters, the [3,3]-rearrangement of propargylic acetates leading to the formation of conjugated enones and substituted indenes, and the rearrangement of allylic acetates. These studies revealed a strong solvent effect on the catalytic activity with 1,2-dichloroethane as the solvent of choice. The screening of Cl and C2 demonstrated only slightly diminished activities in comparison to [Au(NHC)(L)] complexes bearing bulky ligands such as IPr and SIPr.
Keywords
EFFICIENT FORMATION, COMPLEXES, REARRANGEMENT, ACETATES, LIGAND, REACTIVITY, CONVERSION, NITRILES, ALCOHOLS, ESTERS

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Chicago
Gomez-Suarez, Adrian, Ruben S Ramon, Olivier Songis, Alexandra MZ Slawin, Catherine Cazin, and Steven Nolan. 2011. “Influence of a Very Bulky N-heterocyclic Carbene in Gold-mediated Catalysis.” Organometallics 30 (20): 5463–5470.
APA
Gomez-Suarez, A., Ramon, R. S., Songis, O., Slawin, A. M., Cazin, C., & Nolan, S. (2011). Influence of a very bulky N-heterocyclic carbene in gold-mediated catalysis. ORGANOMETALLICS, 30(20), 5463–5470.
Vancouver
1.
Gomez-Suarez A, Ramon RS, Songis O, Slawin AM, Cazin C, Nolan S. Influence of a very bulky N-heterocyclic carbene in gold-mediated catalysis. ORGANOMETALLICS. 2011;30(20):5463–70.
MLA
Gomez-Suarez, Adrian et al. “Influence of a Very Bulky N-heterocyclic Carbene in Gold-mediated Catalysis.” ORGANOMETALLICS 30.20 (2011): 5463–5470. Print.
@article{8168996,
  abstract     = {The syntheses of the free carbene IPr* (IPr* = 1,3-bis (2,6-b is (diphenylmethyl)-4-methylphenyl)imidazol-2-ylidene) and related gold complexes [Au(IPr*)Cl] (C1) and [Au(IPr*)(NTf2)] (C2) were achieved in high yields. The % V-Bur of IPr* for both gold complexes was measured, revealing IPr* as one of the bulkiest NHCs on gold complexes reported to date. In addition, the catalytic activity of C1 and C2 in several reactions, typically catalyzed by Au-I complexes, was investigated. Examples include the tandem alkoxylation/lactonization of gamma-hydroxy-alpha,beta-acetylenic esters, the [3,3]-rearrangement of propargylic acetates leading to the formation of conjugated enones and substituted indenes, and the rearrangement of allylic acetates. These studies revealed a strong solvent effect on the catalytic activity with 1,2-dichloroethane as the solvent of choice. The screening of Cl and C2 demonstrated only slightly diminished activities in comparison to [Au(NHC)(L)] complexes bearing bulky ligands such as IPr and SIPr.},
  author       = {Gomez-Suarez, Adrian and Ramon, Ruben S and Songis, Olivier and Slawin, Alexandra MZ and Cazin, Catherine and Nolan, Steven},
  issn         = {0276-7333},
  journal      = {ORGANOMETALLICS},
  keywords     = {EFFICIENT FORMATION,COMPLEXES,REARRANGEMENT,ACETATES,LIGAND,REACTIVITY,CONVERSION,NITRILES,ALCOHOLS,ESTERS},
  language     = {eng},
  number       = {20},
  pages        = {5463--5470},
  title        = {Influence of a very bulky N-heterocyclic carbene in gold-mediated catalysis},
  url          = {http://dx.doi.org/10.1021/om200705y},
  volume       = {30},
  year         = {2011},
}

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