Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 45, Pages 14155-14158Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201608807
Keywords
-arylethenesulfonyl fluorides; ethenesulfonyl fluoride; Heck-Matsuda reaction; Michael addition; sulfur(VI) fluoride exchange (SuFEx)
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Funding
- National Institutes of Health [R01 GM117145]
- Wuhan University of Technology
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A Heck-Matsuda process for the synthesis of the otherwise difficult to access compounds, -arylethenesulfonyl fluorides, is described. Ethenesulfonyl fluoride (i.e., vinylsulfonyl fluoride, or ESF) undergoes -arylation with stable and readily prepared arenediazonium tetrafluoroborates in the presence of the catalyst palladium(II) acetate to afford the E-isomer sulfonyl analogues of cinnamoyl fluoride in 43-97% yield. The -arylethenesulfonyl fluorides are found to be selectively addressable bis-electrophiles for sulfur(VI) fluoride exchange (SuFEx) click chemistry, in which either the alkenyl moiety or the sulfonyl fluoride group can be the exclusive site of nucleophilic attack under defined conditions, making these rather simple cores attractive for covalent drug discovery.
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