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

Ming Zhong Wang, Man Kin Wong, Chi Ming Che

Research output: Journal article publicationJournal articleAcademic researchpeer-review

104 Citations (Scopus)

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 [(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. KGaA.
Original languageEnglish
Pages (from-to)8353-8364
Number of pages12
JournalChemistry - A European Journal
Volume14
Issue number27
DOIs
Publication statusPublished - 19 Sep 2008
Externally publishedYes

Keywords

  • C - C coupling
  • Gold
  • Homogeneous catalysis
  • Hydroarylation
  • Synthetic methods

ASJC Scopus subject areas

  • Chemistry(all)

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