N-heterocyclic-carbene-catalyzed synthesis of 2-aryl indoles

M. Todd Hovey, Christopher T. Check, Alexandra F. Sipher, Karl A. Scheidt

Research output: Contribution to journalArticlepeer-review

63 Scopus citations

Abstract

A convergent and efficient transition-metal-free catalytic synthesis of 2-aryl-indoles has been developed. The interception of a highly reactive and transient aza-ortho-quinone methide by an acyl anion equivalent generated through N-hetereocyclic carbene catalysis is central to this successful strategy. High yields and a wide scope as well as the streamlined synthesis of a kinase inhibitor are reported. Umpolung: N-heterocyclic carbene catalysis is used for the convergent and efficient transition-metal-free synthesis of 2-aryl-indoles. The interception of a highly reactive and transient aza-ortho-quinone methide by an acyl anion equivalent is central to this successful strategy. The reaction exhibits high yields and a wide scope, and it has been applied to a streamlined synthesis of a kinase inhibitor.

Original languageEnglish (US)
Pages (from-to)9603-9607
Number of pages5
JournalAngewandte Chemie - International Edition
Volume53
Issue number36
DOIs
StatePublished - Sep 1 2014

Keywords

  • asymmetric synthesis
  • carbenes
  • cooperative effects

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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