Metal-free synthesis of fluorinated indoles enabled by oxidative dearomatization

Edon Vitaku, David T. Smith, Jon T Njardarson

Research output: Contribution to journalArticle

16 Scopus citations

Abstract

Nitrogen heterocycles are found in a majority of approved small-molecule pharmaceuticals, and the number of approved fluorinated drugs is increasing each decade. Therefore, new approaches for accessing fluorinated nitrogen heterocycles are of great significance. A novel, scalable, and metal-free method for accessing a wide range of fluorinated indoles is described. This oxidative-dearomatization-enabled approach assembles 2-trifluoromethyl NH-indole products from simple commercially available anilines with hexafluoroacetylacetone in the presence of an organic oxidant. The nature of the aniline N-capping group is critical for the success of this new reaction. Furthermore, the indole products contain a 3-trifluoroacetyl group, which can be exploited to access a plethora of useful functional groups.

Original languageEnglish (US)
Pages (from-to)2243-2247
Number of pages5
JournalAngewandte Chemie - International Edition
Volume55
Issue number6
DOIs
StatePublished - Feb 5 2016

Keywords

  • Dearomatization
  • fluorine
  • indoles
  • nitrogen heterocycle
  • synthetic methods

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis

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