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Mechanism of the [(NHC)Au-I]-catalyzed rearrangement of allylic acetates : a DFT study

(2009) ORGANIC LETTERS. 11(1). p.81-84
Author
Organization
Abstract
The DFT study of the mechanism of the rearrangement of H2C=CHC(CH3)OCOCH3 to (CH3)(H)C=CHCH2OCOCH3 catalyzed by [(NHC)Au](+) (NHC = N-heterocyclic carbene) shows that a low energy path exists, with a barrier of 14.2 kcal.mol(-1), going through a six-membered ring acetoxonium Intermediate and where gold coordinates one of the carbon atoms In the alkene system. The qualitative features of the mechanism are not affected by the Introduction of other NHC ligands, counterions, or solvation effects.
Keywords
GOLD CATALYSIS, HETEROCYCLIC CARBENES, PROPARGYLIC ESTERS, CYCLOPROPANATION, ACTIVATION, ACCESS, SHIFTS, TANDEM

Citation

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MLA
Gourlaouen, Christophe et al. “Mechanism of the [(NHC)Au-I]-catalyzed Rearrangement of Allylic Acetates : a DFT Study.” ORGANIC LETTERS 11.1 (2009): 81–84. Print.
APA
Gourlaouen, C., Marion, N., Nolan, S., & Maseras, F. (2009). Mechanism of the [(NHC)Au-I]-catalyzed rearrangement of allylic acetates : a DFT study. ORGANIC LETTERS, 11(1), 81–84.
Chicago author-date
Gourlaouen, Christophe, Nicolas Marion, Steven Nolan, and Feliu Maseras. 2009. “Mechanism of the [(NHC)Au-I]-catalyzed Rearrangement of Allylic Acetates : a DFT Study.” Organic Letters 11 (1): 81–84.
Chicago author-date (all authors)
Gourlaouen, Christophe, Nicolas Marion, Steven Nolan, and Feliu Maseras. 2009. “Mechanism of the [(NHC)Au-I]-catalyzed Rearrangement of Allylic Acetates : a DFT Study.” Organic Letters 11 (1): 81–84.
Vancouver
1.
Gourlaouen C, Marion N, Nolan S, Maseras F. Mechanism of the [(NHC)Au-I]-catalyzed rearrangement of allylic acetates : a DFT study. ORGANIC LETTERS. 2009;11(1):81–4.
IEEE
[1]
C. Gourlaouen, N. Marion, S. Nolan, and F. Maseras, “Mechanism of the [(NHC)Au-I]-catalyzed rearrangement of allylic acetates : a DFT study,” ORGANIC LETTERS, vol. 11, no. 1, pp. 81–84, 2009.
@article{8169572,
  abstract     = {The DFT study of the mechanism of the rearrangement of H2C=CHC(CH3)OCOCH3 to (CH3)(H)C=CHCH2OCOCH3 catalyzed by [(NHC)Au](+) (NHC = N-heterocyclic carbene) shows that a low energy path exists, with a barrier of 14.2 kcal.mol(-1), going through a six-membered ring acetoxonium Intermediate and where gold coordinates one of the carbon atoms In the alkene system. The qualitative features of the mechanism are not affected by the Introduction of other NHC ligands, counterions, or solvation effects.},
  author       = {Gourlaouen, Christophe and Marion, Nicolas and Nolan, Steven and Maseras, Feliu},
  issn         = {1523-7060},
  journal      = {ORGANIC LETTERS},
  keywords     = {GOLD CATALYSIS,HETEROCYCLIC CARBENES,PROPARGYLIC ESTERS,CYCLOPROPANATION,ACTIVATION,ACCESS,SHIFTS,TANDEM},
  language     = {eng},
  number       = {1},
  pages        = {81--84},
  title        = {Mechanism of the [(NHC)Au-I]-catalyzed rearrangement of allylic acetates : a DFT study},
  url          = {http://dx.doi.org/10.1021/ol802430m},
  volume       = {11},
  year         = {2009},
}

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