Please use this identifier to cite or link to this item: http://hdl.handle.net/10397/21518
Title: Gold(I)-catalyzed intermolecular hydroarylation of alkenes with indoles under thermal and microwave-assisted conditions
Authors: Wang, MZ
Wong, MK 
Che, CM
Keywords: C-C coupling
Gold
Homogeneous catalysis
Hydroarylation
Synthetic methods
Issue Date: 2008
Publisher: Wiley-VCH
Source: Chemistry - a European journal, 2008, v. 14, no. 27, p. 8353-8364 How to cite?
Journal: Chemistry - a European journal 
Abstract: 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 °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[DOUBLE BOND]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.
URI: http://hdl.handle.net/10397/21518
ISSN: 0947-6539
EISSN: 1521-3765
DOI: 10.1002/chem.200800040
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