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Cyclization of 2‐Alkynylallyl Alcohols to Highly Substituted Furans by Gold(I)–Carbene Complexes
Author(s) -
Hashmi A. Stephen K.,
Häffner Tobias,
Rudolph Matthias,
Rominger Frank
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201001479
Subject(s) - carbene , chemistry , sonogashira coupling , catalysis , aryl , alkyl , organic chemistry , combinatorial chemistry , medicinal chemistry , palladium
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.