Metal-Free Synthesis of Functional 1-Substituted-1,2,3-Triazoles from Ethenesulfonyl Fluoride and Organic Azides

Giel, M. C., Smedley, C. J., Mackie, E. R. R., Guo, T., Dong, J., Soares da Costa, T. P., Moses, J. E. (January 2020) Metal-Free Synthesis of Functional 1-Substituted-1,2,3-Triazoles from Ethenesulfonyl Fluoride and Organic Azides. Angew Chem Int Ed Engl, 59 (3). pp. 1181-1186. ISSN 1433-7851

URL: https://pubmed.ncbi.nlm.nih.gov/31709653
DOI: 10.1002/anie.201912728

Abstract

The boom in growth of 1,4-disubstituted triazole products, in particular, since the early 2000's, can be largely attributed to the birth of click chemistry and the discovery of the Cu(I) -catalyzed azide-alkyne cycloaddition (CuAAC). Yet the synthesis of relatively simple, albeit important, 1-substituted-1,2,3-triazoles has been surprisingly more challenging. Reported here is a straightforward and scalable click-inspired protocol for the synthesis of 1-substituted-1,2,3-triazoles from organic azides and the bench stable acetylene surrogate ethenesulfonyl fluoride (ESF). The new transformation tolerates a wide selection of substrates and proceeds smoothly under metal-free conditions to give the products in excellent yield. Under controlled acidic conditions, the 1-substituted-1,2,3-triazole products undergo a Michael addition reaction with a second equivalent of ESF to give the unprecedented 1-substituted triazolium sulfonyl fluoride salts.

Item Type: Paper
Additional Information: Angewandte Chemie (International ed. in English)
CSHL Authors:
Communities: CSHL labs > Moses lab
Depositing User: Matthew Dunn
Date: 13 January 2020
Date Deposited: 08 Jan 2021 17:20
Last Modified: 08 Jan 2021 17:20
Related URLs:
URI: https://repository.cshl.edu/id/eprint/39588

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