One-pot synthesis of substituted indoles via titanium(iv) alkoxide mediated imine formation-copper-catalyzed N-arylation

Ferdinand S. Melkonyan*, Daniil E. Kuznetsov, Marina A. Yurovskaya, Alexander V. Karchava

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

21 Scopus citations

Abstract

Readily accessible o-bromobenzylketones and primary alkyl amines and anilines were used for the construction of substituted indoles in good to excellent yields. The sequence involves a titanium-mediated reaction of ketones with amines to afford imines and subsequent intramolecular cyclization into indoles employing copper catalysis. The two-step protocol allows for the preparation of indoles bearing both N-alkyl and N-aryl groups as well as N-unsubstituted indoles without isolation of the intermediates and is tolerant of a wide range of functionality.

Original languageEnglish (US)
Pages (from-to)8388-8397
Number of pages10
JournalRSC Advances
Volume3
Issue number22
DOIs
StatePublished - Jan 1 2013

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

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