1-Bromoethene-1-sulfonyl fluoride (BESF) is another good connective hub for SuFEx click chemistry
Date
2018
Authors
Smedley, C.J.
Giel, M.C.
Molino, A.
Barrow, A.S.
Wilson, D.J.D.
Moses, J.E.
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Journal article
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Chemical Communications, 2018; 54(47):6020-6023
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Christopher J. Smedley, Marie-Claire Giel, Andrew Molino, Andrew S. Barrow, David J. D. Wilson and John E. Moses
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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-1H1,2,3-triazole-4-sulfonyl fluorides, 2-amino-1-bromoethane-1-sulfonyl fluorides and 4-bromo-b-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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© The Royal Society of Chemistry 2018