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Article: Gold(I)-catalyzed intermolecular hydroarylation of alkenes with indoles under thermal and microwave-assisted conditions

TitleGold(I)-catalyzed intermolecular hydroarylation of alkenes with indoles under thermal and microwave-assisted conditions
Authors
KeywordsC - C coupling
Gold
Homogeneous catalysis
Hydroarylation
Synthetic methods
Issue Date2008
PublisherWiley - V C H Verlag GmbH & Co KGaA. The Journal's web site is located at http://www.wiley-vch.de/home/chemistry
Citation
Chemistry - A European Journal, 2008, v. 14 n. 27, p. 8353-8364 How to Cite?
AbstractAn 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 [(PR 3)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 deuteriumlabeling experiments, a reaction mechanism involving nucleophilic attack of Au(I)-coordinated alkenes by indoles is proposed. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
Persistent Identifierhttp://hdl.handle.net/10722/58437
ISSN
2015 Impact Factor: 5.771
2015 SCImago Journal Rankings: 2.323
ISI Accession Number ID
Funding AgencyGrant Number
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, ChinaAoE/P-10/01
Funding Information:

We are thankful for the financial support of The University of Hong Kong (University Development Fund). Hong Kong Research Grant Council (HKU 7052/07P). and the Areas of Excellence Scheme established under the University Grants Committee of the Hong Kong Special Administrative Region, China (AoE/P-10/01).

References
Grants

 

DC FieldValueLanguage
dc.contributor.authorWang, MZen_HK
dc.contributor.authorWong, MKen_HK
dc.contributor.authorChe, CMen_HK
dc.date.accessioned2010-05-31T03:30:17Z-
dc.date.available2010-05-31T03:30:17Z-
dc.date.issued2008en_HK
dc.identifier.citationChemistry - A European Journal, 2008, v. 14 n. 27, p. 8353-8364en_HK
dc.identifier.issn0947-6539en_HK
dc.identifier.urihttp://hdl.handle.net/10722/58437-
dc.description.abstractAn 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 [(PR 3)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 deuteriumlabeling experiments, a reaction mechanism involving nucleophilic attack of Au(I)-coordinated alkenes by indoles is proposed. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.en_HK
dc.languageengen_HK
dc.publisherWiley - V C H Verlag GmbH & Co KGaA. The Journal's web site is located at http://www.wiley-vch.de/home/chemistryen_HK
dc.relation.ispartofChemistry - A European Journalen_HK
dc.subjectC - C couplingen_HK
dc.subjectGolden_HK
dc.subjectHomogeneous catalysisen_HK
dc.subjectHydroarylationen_HK
dc.subjectSynthetic methodsen_HK
dc.titleGold(I)-catalyzed intermolecular hydroarylation of alkenes with indoles under thermal and microwave-assisted conditionsen_HK
dc.typeArticleen_HK
dc.identifier.emailChe, CM:cmche@hku.hken_HK
dc.identifier.authorityChe, CM=rp00670en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1002/chem.200800040en_HK
dc.identifier.pmid18666293-
dc.identifier.scopuseid_2-s2.0-53849116846en_HK
dc.identifier.hkuros155969en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-53849116846&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume14en_HK
dc.identifier.issue27en_HK
dc.identifier.spage8353en_HK
dc.identifier.epage8364en_HK
dc.identifier.isiWOS:000259913900032-
dc.publisher.placeGermanyen_HK
dc.relation.projectInstitute of molecular technology for drug discovery and synthesis-
dc.identifier.scopusauthoridWang, MZ=24328900000en_HK
dc.identifier.scopusauthoridWong, MK=7403908449en_HK
dc.identifier.scopusauthoridChe, CM=7102442791en_HK

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