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Highly efficient gold(I)-catalyzed regio- and stereoselective hydrocarboxylation of internal alkynes

(2015) ACS CATALYSIS. 5(11). p.6918-6921
Author
Organization
Abstract
We report the highly efficient gold-catalyzed hydrocarboxylation of internal alkynes that operates under solvent- and silver-free conditions. This new, simple, and eco-friendly protocol allows for the synthesis of a wide variety of functionalized aryl and alkyl enol esters in high yields, with Z-stereospecificity and good regioselectivities and without the requirement for purification by chromatography. This process represents an expedient, operationally simple method for the synthesis of enol esters.
Keywords
gold catalysis, carboxylic acids, internal alkynes, N-heterocyclic carbenes, cooperativity, ACETYLENIC CARBOXYLIC-ACIDS, GOLD-CATALYZED SYNTHESIS, N-HETEROCYCLIC CARBENES, VINYL ESTERS, ENOL ESTERS, SELECTIVE CYCLOISOMERIZATION, INTRAMOLECULAR CYCLIZATION, ANTI-MARKOVNIKOV, GAMMA-ALKYLIDENE, SILVER-FREE

Citation

Please use this url to cite or link to this publication:

MLA
Dupuy, Stephanie, et al. “Highly Efficient Gold(I)-Catalyzed Regio- and Stereoselective Hydrocarboxylation of Internal Alkynes.” ACS CATALYSIS, vol. 5, no. 11, 2015, pp. 6918–21.
APA
Dupuy, S., Gasperini, D., & Nolan, S. (2015). Highly efficient gold(I)-catalyzed regio- and stereoselective hydrocarboxylation of internal alkynes. ACS CATALYSIS, 5(11), 6918–6921.
Chicago author-date
Dupuy, Stephanie, Danila Gasperini, and Steven Nolan. 2015. “Highly Efficient Gold(I)-Catalyzed Regio- and Stereoselective Hydrocarboxylation of Internal Alkynes.” ACS CATALYSIS 5 (11): 6918–21.
Chicago author-date (all authors)
Dupuy, Stephanie, Danila Gasperini, and Steven Nolan. 2015. “Highly Efficient Gold(I)-Catalyzed Regio- and Stereoselective Hydrocarboxylation of Internal Alkynes.” ACS CATALYSIS 5 (11): 6918–6921.
Vancouver
1.
Dupuy S, Gasperini D, Nolan S. Highly efficient gold(I)-catalyzed regio- and stereoselective hydrocarboxylation of internal alkynes. ACS CATALYSIS. 2015;5(11):6918–21.
IEEE
[1]
S. Dupuy, D. Gasperini, and S. Nolan, “Highly efficient gold(I)-catalyzed regio- and stereoselective hydrocarboxylation of internal alkynes,” ACS CATALYSIS, vol. 5, no. 11, pp. 6918–6921, 2015.
@article{8168264,
  abstract     = {We report the highly efficient gold-catalyzed hydrocarboxylation of internal alkynes that operates under solvent- and silver-free conditions. This new, simple, and eco-friendly protocol allows for the synthesis of a wide variety of functionalized aryl and alkyl enol esters in high yields, with Z-stereospecificity and good regioselectivities and without the requirement for purification by chromatography. This process represents an expedient, operationally simple method for the synthesis of enol esters.},
  author       = {Dupuy, Stephanie and Gasperini, Danila and Nolan, Steven},
  issn         = {2155-5435},
  journal      = {ACS CATALYSIS},
  keywords     = {gold catalysis,carboxylic acids,internal alkynes,N-heterocyclic carbenes,cooperativity,ACETYLENIC CARBOXYLIC-ACIDS,GOLD-CATALYZED SYNTHESIS,N-HETEROCYCLIC CARBENES,VINYL ESTERS,ENOL ESTERS,SELECTIVE CYCLOISOMERIZATION,INTRAMOLECULAR CYCLIZATION,ANTI-MARKOVNIKOV,GAMMA-ALKYLIDENE,SILVER-FREE},
  language     = {eng},
  number       = {11},
  pages        = {6918--6921},
  title        = {Highly efficient gold(I)-catalyzed regio- and stereoselective hydrocarboxylation of internal alkynes},
  url          = {http://dx.doi.org/10.1021/acscatal.5b02090},
  volume       = {5},
  year         = {2015},
}

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