Smedley, C. J., Giel, M. C., Molino, A., Barrow, A. S., Wilson, D. J. D., Moses, J. E. (June 2018) 1-Bromoethene-1-sulfonyl fluoride (BESF) is another good connective hub for SuFEx click chemistry. Chem Commun (Camb), 54 (47). pp. 6020-6023. ISSN 1359-7345
Abstract
We demonstrate 1,2-dibromoethane-1-sulfonyl fluoride (DESF) as a bench-stable and readily accessible precursor to the robust SuFEx connector, 1-bromoethene-1-sulfonyl fluoride (BESF). The in situ generation of BESF from DESF opens up several new reaction profiles, including application in the syntheses of unprecedented 3-substituted isoxazole-5-sulfonyl fluorides, 1-substituted-1H-1,2,3-triazole-4-sulfonyl fluorides, 2-amino-1-bromoethane-1-sulfonyl fluorides and 4-bromo-β-sultams in good to excellent yields. These new modules comprise a pendant sulfonyl fluoride handle, which further undergoes facile and selective SuFEx reactions with a selection of aryl silyl ethers to generate stable and useful sulfonate connections.
| Item Type: | Paper |
|---|---|
| Additional Information: | Chemical communications (Cambridge, England) |
| CSHL Authors: | |
| Communities: | CSHL labs > Moses lab |
| Depositing User: | Matthew Dunn |
| Date: | 8 June 2018 |
| Date Deposited: | 08 Jan 2021 17:26 |
| Last Modified: | 08 Jan 2021 17:26 |
| URI: | https://repository.cshl.edu/id/eprint/39575 |
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