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Various 2‐alkynylallyl alcohols were synthesized by a generally applicable Sonogashira coupling protocol. Subsequent gold‐catalyzed transformation was investigated. The use of Au I catalysts bearing carbene ligands, of either the N‐heterocyclic carbene or nitrogen acyclic carbene type, delivered the desired products with low catalyst loadings and under very mild reaction conditions. A broad array of substrates was tested, including alkyl‐, alkenyl‐, and aryl‐substituted alkynes, as well as substrates with two alkynyl moieties. The methodology turned out to have a broad scope. Secondary allyl alcohols were also tolerated, and the resulting trisubstituted furans could be isolated in high yields.
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Hashmi et al. (2010) studied this question.
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