Ethenesulfonyl Fluoride: The Most Perfect Michael Acceptor Ever Found?
Angew. Chem. Int. Ed. 2016, 55, 12664-12667 Angew. Chem. Int. Ed.
Angew. Chem. 2016, 128, 12854-12858 Angew. Chem.
The kinetics of the reactions of ethenesulfonyl fluoride (ESF) with sulfonium and pyridinium ylides were measured photometrically to determine the electrophilicity parameter of ESF according to the correlation lg k20 °C=sN(N+E). With E=−12.09, ESF is among the strongest Michael acceptors in our comprehensive electrophilicity scale, which explains its excellent performance in reactions with many nucleophiles. Its predicted usability as a reagent in electrophilic aromatic substitutions with electron-rich arenes was confirmed by uncatalyzed reactions with alkyl-substituted pyrroles.