Umpolung reactivity of indole through gold catalysis

Biao Lu, Yingdong Luo, Lianzhu Liu, Longwu Ye, Yanzhao Wang, Liming Zhang

Research output: Contribution to journalArticlepeer-review

172 Scopus citations

Abstract

Electrophilic indole? Indoles, which are typically nucleophilic, can be made electrophilic through gold catalysis. By using an ortho-azido group to deliver a nitrene intramolecularly, an arylalkyne is converted into a gold carbene intermediate containing an indole skeleton that is highly electrophilic at the 3-position. A range of functionalized indoles is readily accessed by utilizing this strategy.

Original languageEnglish (US)
Pages (from-to)8358-8362
Number of pages5
JournalAngewandte Chemie - International Edition
Volume50
Issue number36
DOIs
StatePublished - Aug 29 2011

Keywords

  • catalysis
  • gold
  • indole
  • nitrenes
  • umpolung

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