Site-selective deuteration of N-heterocycles via iridium-catalyzed hydrogen isotope exchange

William J. Kerr, David M. Lindsay, Philippa K. Owens, Marc Reid, Tell Tuttle, Sébastien Campos

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Abstract

The application of iridium(I) NHC/phosphine catalysts has delivered highly selective deuteration of indole, azaindole, and pyrrole N-heterocycles, which represent an important and relatively underexplored class of labeling substrates. Common N-protecting groups have been used to selectively direct C–H activation, and can be removed under mild conditions with retention of the deuterium label. The method is exemplified by the labeling of drug molecule Sumatriptan. Complementary DFT studies have been conducted to facilitate the rationalization of the very good selectivity offered by the mild and convenient labeling process.
Original languageEnglish
Pages (from-to)7182–7186
Number of pages5
JournalACS Catalysis
Volume7
Issue number10
Early online date11 Sep 2017
DOIs
Publication statusPublished - 6 Oct 2017

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Keywords

  • iridium
  • catalysis
  • indoles
  • isotope labeling
  • C-H activation
  • heterocycles

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