NH-Heterocyclic Aryliodonium Salts and their Selective Conversion into N1-Aryl-5-iodoimidazoles

Yichen Wu, Susana Izquierdo, Pietro Vidossich, Agustí Lledós, Alexandr Shafir

Research output: Contribution to journalArticleResearchpeer-review

22 Citations (Scopus)

Abstract

© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim The synthesis of N-arylimidazoles substituted at the sterically encumbered 5-position is a challenge for modern synthetic approaches. A new family of imidazolyl aryliodonium salts is reported, which serve as a stepping stone on the way to selective formation of N1-aryl-5-iodoimidazoles. Iodine acts as a “universal” placeholder poised for replacement by aryl substituents. These new λ3-iodanes are produced by treating the NH-imidazole with ArI(OAc)2, and are converted to N1-aryl-5-iodoimidazoles by a selective copper-catalyzed aryl migration. The method tolerates a variety of aryl fragments and is also applicable to substituted imidazoles.
Original languageEnglish
Pages (from-to)7152-7156
JournalAngewandte Chemie - International Edition
Volume55
Issue number25
DOIs
Publication statusPublished - 1 Jan 2016

Keywords

  • copper catalysis
  • C−H functionalization
  • C−N coupling
  • hypervalent iodine
  • imidazoles

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