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Synfacts 2011(9): 1005-1005  
DOI: 10.1055/s-0030-1260880
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of 1,5-Substituted Sulfonyl Triazoles

Contributor(s): Paul Knochel, Thomas Kunz
M. E. Meza-Aviña, M. K. Pater, C. B. Lee, T. J. Dietz, M. P. Croatt*
University of North Carolina at Greensboro, USA
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Publication History

Publication Date:
19 August 2011 (online)

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Significance

Herein, the preparation of 1,5-substituted sulfonyl triazoles from lithium acetylides and sulfonyl azides is described. This protocol is complementary to the copper-catalyzed azide-alkyne cycloaddition giving a 1,4-substitution pattern. Both substrates are readily available and the reaction proceeds for a range of terminal alkynes. Furthermore, trapping the intermediary triazole anion with electrophiles affords 1,4,5-substituted triazoles in moderate to good yields.