Synthesis of 3,3′-Disubstituted Indolenines Utilizing the Lewis Acid Catalyzed Alkylation of 2,3-Disubstituted Indoles with Trichloroacetimidates

Arijit A. Adhikari, Léa Radal, John D. Chisholm

Research output: Contribution to journalArticle

5 Scopus citations

Abstract

Trichloroacetimidates function as effective electrophiles for the selective C3-alkylation of 2,3-disubstituted indoles to provide 3,3′-disubstituted indolenines. These indolenines are common synthetic intermediates that are often utilized in the synthesis of complex molecules. Effective reaction conditions utilizing Lewis acid catalysts have been determined, and the scope of the reaction with respect to indole and imidate reaction partner has been investigated. This chemistry provides an alternative to base promoted and transition-metal-catalyzed methods that are more commonly utilized to access similar indolenines.

Original languageEnglish (US)
Article numberst-2017-r0343-l
Pages (from-to)2335-2339
Number of pages5
JournalSynlett
Volume28
Issue number17
DOIs
StatePublished - Oct 23 2017

Keywords

  • Lewis acid
  • alkylation
  • catalysis
  • indole
  • indolenine
  • trichloroacetimidate

ASJC Scopus subject areas

  • Organic Chemistry

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