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

244 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

Triazoles
Azides
Cycloaddition
Chlorine compounds
Copper
Catalysts
Alkynes
Chloroform
ketenimine
2,6-lutidine

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

Copper-catalyzed synthesis of N-sulfonyl-1,2,3-triazoles : Controlling selectivity. / Yoo, Eun Jeong; Ahlquist, Mårten; Kim, Seok Hwan; Bae, Imhyuck; Fokin, Valery V.; Sharpless, K. Barry; Chang, Sukbok.

In: Angewandte Chemie - International Edition, Vol. 46, No. 10, 2007, p. 1730-1733.

Research output: Contribution to journalArticle

Yoo, EJ, Ahlquist, M, Kim, SH, Bae, I, Fokin, VV, Sharpless, KB & Chang, S 2007, 'Copper-catalyzed synthesis of N-sulfonyl-1,2,3-triazoles: Controlling selectivity', Angewandte Chemie - International Edition, vol. 46, no. 10, pp. 1730-1733. https://doi.org/10.1002/anie.200604241
Yoo, Eun Jeong ; Ahlquist, Mårten ; Kim, Seok Hwan ; Bae, Imhyuck ; Fokin, Valery V. ; Sharpless, K. Barry ; Chang, Sukbok. / Copper-catalyzed synthesis of N-sulfonyl-1,2,3-triazoles : Controlling selectivity. In: Angewandte Chemie - International Edition. 2007 ; Vol. 46, No. 10. pp. 1730-1733.
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