Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 24, Pages 7514-7519Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201400112
Keywords
alkynes; cyclization; gold; heterocycles; rearrangement
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Funding
- National Natural Science Foundation of China [21125210, 21121062, 21372244]
- Chinese Academy of Science
- Major State Basic Research Development Program [2011CB808700]
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A gold-catalyzed cycloisomerization of silyl-protected 2-(1-alkynyl)-2-alken-1-(2-furanyl)-1-ols with various nucleophiles including water, alcohol, aniline, sulfonamide, and electron-rich arene has been developed. The method provides a highly efficient access to 5,7-disubstituted or 2,5,7-trisubstituted benzo[b]furans with a wide diversity of substituents under mild reaction conditions, which are not easily available by other methods. Remarkably, an interesting rearrangement of the alkyl group from C2 to the C3 position of the furan ring takes place during the cyclization process. The following gold-assisted allylic substitution enables an elaboration of benzo[b]furans on its side chain of the C5 position with a wide range of functional groups.
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