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1-Bromoethene-1-sulfonyl fluoride (1-Br-ESF), a new SuFEx clickable reagent, and its application for regioselective construction of 5-sulfonylfluoro isoxazoles
A new fluorosulfonylation reagent 1-bromoethene-1-sulfonyl fluoride was developed (1-Br-ESF). This unique reagent possesses three addressable handles (vinyl, bromide, and sulfonyl fluoride) and has great potential to function as a tris-electrophile and as a sulfur(vi) fluoride exchange (SuFEx) click...
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Published in: | Chemical communications (Cambridge, England) England), 2018, Vol.54 (35), p.4477-4480 |
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Main Authors: | , |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
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Summary: | A new fluorosulfonylation reagent 1-bromoethene-1-sulfonyl fluoride was developed (1-Br-ESF). This unique reagent possesses three addressable handles (vinyl, bromide, and sulfonyl fluoride) and has great potential to function as a tris-electrophile and as a sulfur(vi) fluoride exchange (SuFEx) clickable material to enrich the SuFEx tool cabinet. The application of this reagent for regioselective synthesis of 5-sulfonylfluoro isoxazoles has been realized through a [3+2] cycloaddition with N-hydroxybenzimidoyl chlorides. This practical protocol provides a general and direct route to functionalized isoxazoles possessing sulfonyl fluoride moieties. |
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ISSN: | 1359-7345 1364-548X |
DOI: | 10.1039/c8cc00986d |