A Heck-Matsuda Process for the Synthesis of ß-Arylethenesulfonyl Fluorides: Selectively Addressable Bis-electrophiles for SuFEx Click Chemistry.
Angew Chem Int Ed Engl
; 55(45): 14155-14158, 2016 11 02.
Article
em En
| MEDLINE
| ID: mdl-27723200
ABSTRACT
A Heck-Matsuda process for the synthesis of the otherwise difficult to access compounds, ß-arylethenesulfonyl fluorides, is described. Ethenesulfonyl fluoride (i.e., vinylsulfonyl fluoride, or ESF) undergoes ß-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 ß-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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1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Ácidos Sulfínicos
/
Etilenos
Idioma:
En
Ano de publicação:
2016
Tipo de documento:
Article