A Heck–Matsuda Process for the Synthesis of β‐Arylethenesulfonyl Fluorides: Selectively Addressable Bis‐electrophiles for SuFEx Click Chemistry |
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| Authors: | Prof Hua‐Li Qin Qinheng Zheng Dr Grant A L Bare Prof Peng Wu Prof K Barry Sharpless |
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| Institution: | 1. Department of Chemistry, The Scripps Research Institute, La Jolla, CA, USA;2. School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, Wuhan, Hubei Province, China;3. Department of Chemical Physiology, The Scripps Research Institute, La Jolla, CA, USA |
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| Abstract: | A Heck–Matsuda process for the synthesis of the otherwise difficult to access compounds, β‐arylethenesulfonyl fluorides, is described. Ethenesulfonyl fluoride (i.e., vinylsulfonyl fluoride, or ESF) undergoes β‐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 β‐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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| Keywords: | β -arylethenesulfonyl fluorides ethenesulfonyl fluoride Heck– Matsuda reaction Michael addition sulfur(VI) fluoride exchange (SuFEx) |
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