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A Heck-Matsuda Process for the Synthesis of [beta]-Arylethenesulfonyl Fluorides: Selectively Addressable Bis-electrophiles for SuFEx Click Chemistry

Qin, Hua-Li ; Zheng, Qinheng ; Bare, Grant A L ; Wu, Peng ; Sharpless, K Barry

Angewandte Chemie (International ed.), 2016-11, Vol.55 (45), p.14155 [Periódico revisado por pares]

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Título:
A Heck-Matsuda Process for the Synthesis of [beta]-Arylethenesulfonyl Fluorides: Selectively Addressable Bis-electrophiles for SuFEx Click Chemistry
Autor: Qin, Hua-Li ; Zheng, Qinheng ; Bare, Grant A L ; Wu, Peng ; Sharpless, K Barry
Assuntos: Fluorides
É parte de: Angewandte Chemie (International ed.), 2016-11, Vol.55 (45), p.14155
Descrição: A Heck-Matsuda process for the synthesis of the otherwise difficult to access compounds, [beta]-arylethenesulfonyl fluorides, is described. Ethenesulfonyl fluoride (i.e., vinylsulfonyl fluoride, or ESF) undergoes [beta]-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 [beta]-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.
Editor: Weinheim: Wiley Subscription Services, Inc
Idioma: Inglês

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