Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 75, Issue 11, Pages 3671-3677Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo100378u
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Funding
- National Natural Science Foundation of China [20721003, 20872153]
- International Collaboration Projects [20720102040]
- 863 Hi-Tech Program of China [2006AA020602, 2006AA10A201]
- National S&T Major Projects [2009ZX09501-001, 2009ZX09501-010]
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A regioselective hydroamidation of 2-(1-alkynyl)phenylacetamides with Au(PPh3)Cl/AgSbF6 as the catalyst proceeded by a 7-endo-dig pathway to afford 3-benzazepinones. This method accommodates a broad range of alkyl and aryl alkynyl substitutes in moderate to high yields (63-91%). Moreover, unexpectedly, we also discovered a gold-mediated transformation from 2-(1-alkynyl)phenylacetamides to 5-bromo-3-benzazepinones, and AuBr3 was found to not only play an activation role but also act as a reactant in the reaction for the first time.
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