Highly Efficient Gold(I)-Catalyzed Regio- and Stereoselective Hydrocarboxylation of Internal Alkynes

http://pubs.acs.org/doi/abs/10.1021/acscatal.5b02090

Stéphanie Dupuy†, Danila Gasperini†, and Steven P. Nolan*‡

† EaStCHEM School of Chemistry, University of St. Andrews, North Haugh, St. Andrews, Fife KY16 9ST,U.K.
‡ Chemistry Department, College of Science, King Saud University, Riyadh 11451, Saudi Arabia
ACS Catal., 2015, 5, pp 6918–6921
DOI: 10.1021/acscatal.5b02090
Publication Date (Web): October 12, 2015




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