期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 14, 期 27, 页码 8353-8364出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200800040
关键词
C-C coupling; gold; homogeneous catalysis; hydroarylation; synthetic methods
资金
- The University of Hong Kong (University Development Fund)
- Hong Kong Research Grant Council (HKU) [7052/07P]
- University Grants Committee of the Hong Kong Special Administrative Region, China [AoE/P-10/01]
An efficient method for intermolecular hydroarylation of aryl and aliphatic alkenes with indoles using a combination of [(PR3)AuCl]/AgOTf as catalyst under thermal and microwave-assisted conditions has been developed. The gold(I)-catalyzed reactions of indoles with aryl alkenes were achieved in toluene at 85 degrees C over a reaction time of 1-3 h with 2 mol % of [(PR3)AuCl]/AgOTf as catalyst. This method works for a variety of styrenes bearing electron-deficient, electron-rich, and sterically bulky substituents to give the corresponding products in good to high yields (60-95%). Under microwave irradiation, coupling of unactivated aliphatic alkenes with indoles gave the corresponding adducts in up to 90% yield. Selective hydroarylation of terminal C=C bond of conjugated dienes with indoles gave good product yields (62-81%). On the basis of deuterium-labeling experiments, a reaction mechanism involving nucleophilic attack of Au(I)-coordinated alkenes by indoles is proposed.
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