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https://hdl.handle.net/2440/137056
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Type: | Journal article |
Title: | 1-Bromoethene-1-sulfonyl fluoride (BESF) is another good connective hub for SuFEx click chemistry |
Author: | Smedley, C.J. Giel, M.C. Molino, A. Barrow, A.S. Wilson, D.J.D. Moses, J.E. |
Citation: | Chemical Communications, 2018; 54(47):6020-6023 |
Publisher: | Royal Society of Chemistry (RSC) |
Issue Date: | 2018 |
ISSN: | 1359-7345 1364-548X |
Statement of Responsibility: | Christopher J. Smedley, Marie-Claire Giel, Andrew Molino, Andrew S. Barrow, David J. D. Wilson and John E. Moses |
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. |
Rights: | © The Royal Society of Chemistry 2018 |
DOI: | 10.1039/c8cc03400a |
Grant ID: | http://purl.org/au-research/grants/arc/FT170100156 |
Published version: | http://dx.doi.org/10.1039/c8cc03400a |
Appears in Collections: | Chemistry publications |
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