Copper-catalyzed synthesis of N-sulfonyl-1,2,3-triazoles: Controlling selectivity

Eun Jeong Yoo, Mårten Ahlquist, Seok Hwan Kim, Imhyuck Bae, Valery V. Fokin, K. Barry Sharpless, Sukbok Chang

Research output: Contribution to journalArticle

249 Citations (Scopus)

Abstract

(Chemical Equation Presented) 4-Substituted 1-(N-sulfonyl)-1,2,3-triazoles are selectively obtained by using the Cu-catalyzed azide-alkyne cycloaddition reaction with sulfonyl azides. Performing the reaction at 0°C in chloroform in the presence of 2,6-lutidine and Cul as the catalyst effectively prevents the ketenimine pathway and provides convenient access to N-sulfonyltriazoles in good to excellent yields.

Original languageEnglish
Pages (from-to)1730-1733
Number of pages4
JournalAngewandte Chemie - International Edition
Volume46
Issue number10
DOIs
Publication statusPublished - 2007
Externally publishedYes

    Fingerprint

Keywords

  • Alkynes
  • Copper
  • Cycloaddition
  • Sulfonyl azides
  • Sulfonyltriazoles

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Yoo, E. J., Ahlquist, M., Kim, S. H., Bae, I., Fokin, V. V., Sharpless, K. B., & Chang, S. (2007). Copper-catalyzed synthesis of N-sulfonyl-1,2,3-triazoles: Controlling selectivity. Angewandte Chemie - International Edition, 46(10), 1730-1733. https://doi.org/10.1002/anie.200604241