Cyclization of 2-alkynylallyl alcohols to highly substituted furans by gold(I)-carbene complexes
Various 2-alkynylallyl alcohols were synthesized by a generally applicable Sonogashira coupling protocol. Subsequent gold-catalyzed transformation was investigated. The use of AuI catalysts bearing carbene ligands, of either the N-heterocyclic carbene or nitrogen acyclic carbene type, delivered the...
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| Main Authors: | , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
February 2011
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| In: |
European journal of organic chemistry
Year: 2010, Issue: 4, Pages: 667-671 |
| ISSN: | 1099-0690 |
| DOI: | 10.1002/ejoc.201001479 |
| Online Access: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/ejoc.201001479 Verlag, lizenzpflichtig, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.201001479 
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| Author Notes: | A. Stephen K. Hashmi, Tobias Häffner, Matthias Rudolph, and Frank Rominger |
| Summary: | Various 2-alkynylallyl alcohols were synthesized by a generally applicable Sonogashira coupling protocol. Subsequent gold-catalyzed transformation was investigated. The use of AuI 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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| Item Description: | First published: 27 December 2010 Gesehen am 31.08.2022 |
| Physical Description: | Online Resource |
| ISSN: | 1099-0690 |
| DOI: | 10.1002/ejoc.201001479 |