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On the mechanism of the digold(I)-hydroxide-catalysed hydrophenoxylation of alkynes

(2016) CHEMISTRY-A EUROPEAN JOURNAL. 22(3). p.1125-1132
Author
Organization
Abstract
Herein, we present a detailed investigation of the mechanistic aspects of the dual gold-catalysed hydrophenoxylation of alkynes by both experimental and computational methods. The dissociation of [{Au(NHC)}(2)(mu-OH)][BF4] is essential to enter the catalytic cycle, and this step is favoured by the presence of bulky, non-coordinating counter ions. Moreover, in silico studies confirmed that phenol does not only act as a reactant, but also as a co-catalyst, lowering the energy barriers of several transition states. A gem-diaurated species might form during the reaction, but this lies deep within a potential energy well, and is likely to be an "off-cycle" rather than an "in-cycle" intermediate.
Keywords
alkynes, density functional calculations, gold, homogeneous catalysis, hydrophenoxylation, reaction mechanisms, DUAL GOLD CATALYSIS, OLEFIN METATHESIS, GOLD(I)-CATALYZED HYDROALKOXYLATION, HIGHLY EFFICIENT, SILVER-FREE, BASIS-SETS, COMPLEXES, COUNTERION, CARBENE, PRECATALYSTS

Citation

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MLA
Gomez-Suarez, Adrian, et al. “On the Mechanism of the Digold(I)-Hydroxide-Catalysed Hydrophenoxylation of Alkynes.” CHEMISTRY-A EUROPEAN JOURNAL, vol. 22, no. 3, 2016, pp. 1125–32.
APA
Gomez-Suarez, A., Oonishi, Y., Martin, A. R., Vummaleti, S. V., Nelson, D. J., Cordes, D. B., … Poater, A. (2016). On the mechanism of the digold(I)-hydroxide-catalysed hydrophenoxylation of alkynes. CHEMISTRY-A EUROPEAN JOURNAL, 22(3), 1125–1132.
Chicago author-date
Gomez-Suarez, Adrian, Yoshihiro Oonishi, Anthony R Martin, Sai VC Vummaleti, David J Nelson, David B Cordes, Alexandra MZ Slawin, Luigi Cavallo, Steven Nolan, and Albert Poater. 2016. “On the Mechanism of the Digold(I)-Hydroxide-Catalysed Hydrophenoxylation of Alkynes.” CHEMISTRY-A EUROPEAN JOURNAL 22 (3): 1125–32.
Chicago author-date (all authors)
Gomez-Suarez, Adrian, Yoshihiro Oonishi, Anthony R Martin, Sai VC Vummaleti, David J Nelson, David B Cordes, Alexandra MZ Slawin, Luigi Cavallo, Steven Nolan, and Albert Poater. 2016. “On the Mechanism of the Digold(I)-Hydroxide-Catalysed Hydrophenoxylation of Alkynes.” CHEMISTRY-A EUROPEAN JOURNAL 22 (3): 1125–1132.
Vancouver
1.
Gomez-Suarez A, Oonishi Y, Martin AR, Vummaleti SV, Nelson DJ, Cordes DB, et al. On the mechanism of the digold(I)-hydroxide-catalysed hydrophenoxylation of alkynes. CHEMISTRY-A EUROPEAN JOURNAL. 2016;22(3):1125–32.
IEEE
[1]
A. Gomez-Suarez et al., “On the mechanism of the digold(I)-hydroxide-catalysed hydrophenoxylation of alkynes,” CHEMISTRY-A EUROPEAN JOURNAL, vol. 22, no. 3, pp. 1125–1132, 2016.
@article{8168219,
  abstract     = {Herein, we present a detailed investigation of the mechanistic aspects of the dual gold-catalysed hydrophenoxylation of alkynes by both experimental and computational methods. The dissociation of [{Au(NHC)}(2)(mu-OH)][BF4] is essential to enter the catalytic cycle, and this step is favoured by the presence of bulky, non-coordinating counter ions. Moreover, in silico studies confirmed that phenol does not only act as a reactant, but also as a co-catalyst, lowering the energy barriers of several transition states. A gem-diaurated species might form during the reaction, but this lies deep within a potential energy well, and is likely to be an "off-cycle" rather than an "in-cycle" intermediate.},
  author       = {Gomez-Suarez, Adrian and Oonishi, Yoshihiro and Martin, Anthony R and Vummaleti, Sai VC and Nelson, David J and Cordes, David B and Slawin, Alexandra MZ and Cavallo, Luigi and Nolan, Steven and Poater, Albert},
  issn         = {0947-6539},
  journal      = {CHEMISTRY-A EUROPEAN JOURNAL},
  keywords     = {alkynes,density functional calculations,gold,homogeneous catalysis,hydrophenoxylation,reaction mechanisms,DUAL GOLD CATALYSIS,OLEFIN METATHESIS,GOLD(I)-CATALYZED HYDROALKOXYLATION,HIGHLY EFFICIENT,SILVER-FREE,BASIS-SETS,COMPLEXES,COUNTERION,CARBENE,PRECATALYSTS},
  language     = {eng},
  number       = {3},
  pages        = {1125--1132},
  title        = {On the mechanism of the digold(I)-hydroxide-catalysed hydrophenoxylation of alkynes},
  url          = {http://dx.doi.org/10.1002/chem.201503097},
  volume       = {22},
  year         = {2016},
}

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