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Regioselective Access to Sultam Motifs through Cobalt-Catalyzed Annulation of Aryl Sulfonamides and Alkynes using an 8-Aminoquinoline Directing Group

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84 Citations (Scopus)

Abstract

The use of cobalt as catalyst in direct C-H activation protocols as a replacement for more expensive second row transition metals is currently attracting significant attention. Herein we disclose a facile cobalt-catalyzed C-H functionalization route towards sultam motifs through annulation of easily prepared aryl sulfonamides and alkynes using 8-aminoquinoline as a directing group. The reaction shows broad substrate scope with products obtained in a highly regioselective manner in good to excellent isolated yields. Mechanistic insights suggest the formation of a Co(III)-aryl key species via a rate-determining arene C-H activation during the annulation reaction.

Original languageEnglish
Pages (from-to)4003-4012
Number of pages10
JournalAdvanced Synthesis and Catalysis
Volume357
Issue number18
DOIs
Publication statusPublished - 14 Dec 2015

Keywords

  • C-H activation
  • alkynes
  • annulation
  • cobalt
  • regioselectivity
  • sulfonamides
  • sultams

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