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
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) |
| Subjects: | chemistry chemistry > techniques > click chemistry chemistry > techniques |
| CSHL Authors: | |
| Communities: | CSHL labs > Moses lab |
| Depositing User: | Matthew Dunn |
| Date: | 13 January 2020 |
| Date Deposited: | 08 Jan 2021 17:20 |
| Last Modified: | 30 Jan 2024 20:43 |
| Related URLs: | |
| URI: | https://repository.cshl.edu/id/eprint/39588 |
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