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DOI: 10.1055/s-0029-1218430
A Facile Gold-Catalyzed Synthesis of Heterocycles from Propargyl Alcohols
Contributor(s):Paul Knochel, Andrei GavryushinUniversity of Florida, Gainesville, USA
An Extremely Facile Synthesis of Furans, Pyrroles, and Thiophenes by the Dehydrative Cyclization of Propargyl Alcohols
Org. Lett. 2009, 11: 4624-4627
Publication History
Publication Date:
21 December 2009 (online)
Key words
propargyl alcohols - heterocycles - gold catalysis
Significance
Heterocycles such as furans, pyrroles, and thiophenes are widely spread cores found in biologically active natural products as well as pharmaceuticals and agrochemicals. The herein reported gold-catalyzed cycloisomerization of easily available propargylic alcohols provides a simple access to numerous derivatives of these important heterocycles.
Comment
The reaction proceeds well even in an open vessel without exclusion of air, but at least 2 mol% of the catalyst is needed. Using some precautions, the catalyst loading can be decreased to 0.1 mol% without a significant drop of the yield.
Review: For a review on gold-catalyzed reactions, see: Z. Li, C. Brouwer, C. He Chem. Rev. 2008, 108, 3239-3265.