1-Bromoethene-1-sulfonyl fluoride (BESF) is another good connective hub for SuFEx click chemistry

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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