Journal
ACS CATALYSIS
Volume 3, Issue 12, Pages 3086-3098Publisher
AMER CHEMICAL SOC
DOI: 10.1021/cs4009144
Keywords
gold catalysis; gold complexes; N-heterocyclic carbenes; cycloisomerization; alkynoic acids; enol-lactones; heterocycles
Categories
Funding
- MINECO [CTQ2010-14796/BQU, CTQ2010-17476/BQU, CSD2007-00006]
- Junta de Andalucia of Spain [FQM-3151]
- Centre National de la Recherche Scientifique (CNRS) of France
- MECD of Spain
- European Social Fund
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Zwitterionic imidazolium salts bearing 3-sulfonatopropyl, and 2-pyridyl, 2-picolyl, and 2-pyridylethyl substituents have been synthesized and employed as precursors for the preparation of novel water-soluble Au(I)- and Au(III)-NHC complexes of general composition [AuCl(NHC)] and [AuCl3(NHC)] (NHC = N-heterocyclic carbene), respectively. These complexes proved to be active, selective, and recyclable catalysts for the intramolecular cyclization of gamma-alkynoic acids under biphasic toluene/water conditions, leading to the desired enol-lactones in high yields under mild conditions (r.t.). Remarkably, despite the well-known ability of gold complexes to promote the hydration of C C bonds, the competitive hydration process was not observed, even during the cycloisomerization reactions of 1,6-diynes.
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