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

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

Chemical communications (Cambridge, England) (2018-05-26)
Christopher J Smedley, Marie-Claire Giel, Andrew Molino, Andrew S Barrow, David J D Wilson, John E Moses
ANOTACE

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.

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Sigma-Aldrich
1,2-Dibromoethane-1-sulfonyl fluoride