1-Iodobuta-1,3-diynes in Copper-Catalyzed Azide-Alkyne Cycloaddition: a One-Step Route to 4-Ethynyl-5-iodo-1,2,3-triazoles

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14 Scopus citations

Abstract

Cu-catalyzed 1,3-dipolar cycloaddition of iododiacetylenes with organic azides using iodotris(triphenylphosphine)copper(I) as a catalyst was found to be an efficient one-step synthetic route to 5-iodo-4-ethynyltriazoles. The reaction is tolerant to various functional groups in both butadiyne and azide moieties. The synthetic application of 5-iodo-4-ethynyl triazoles obtained was also evaluated: the Sonogashira coupling with alkynes resulted in unsymmetrically substituted triazole-fused enediyne systems, while the Suzuki reaction yielded the corresponding 5-aryl-4-ethynyl triazoles.

Original languageEnglish
Pages (from-to)1925-1940
Number of pages16
JournalJournal of Organic Chemistry
Volume84
Issue number4
DOIs
StatePublished - 15 Feb 2019

Scopus subject areas

  • Chemistry(all)
  • Organic Chemistry

Keywords

  • ONE-POT SYNTHESIS
  • CLICK-CHEMISTRY
  • REGIOSELECTIVE SYNTHESIS
  • COUPLING REACTION
  • 1,4,5-TRISUBSTITUTED 1,2,3-TRIAZOLES
  • SUBSTITUTED 1,2,3-TRIAZOLES
  • ELECTROPHILIC CYCLIZATION
  • CONVENIENT SYNTHESIS
  • TERMINAL ALKYNES
  • ACID CATALYSIS

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