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Issue 47, 2018
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1-Bromoethene-1-sulfonyl fluoride (BESF) is another good connective hub for SuFEx click chemistry

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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.

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

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Publication details

The article was received on 26 Apr 2018, accepted on 18 May 2018 and first published on 25 May 2018


Article type: Communication
DOI: 10.1039/C8CC03400A
Chem. Commun., 2018,54, 6020-6023

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

    C. J. Smedley, M. Giel, A. Molino, A. S. Barrow, D. J. D. Wilson and J. E. Moses, Chem. Commun., 2018, 54, 6020
    DOI: 10.1039/C8CC03400A

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