We describe a simple and efficient procedure for the synthesis of -vinyl-substituted pyridones from ketones and 2-fluoropyridine in the presence of trifluoromethane sulfonic anhydride, followed by a base treatment. Various ketones with electron-donating or electron-withdrawing groups at the benzene rings can be used in this reaction. A preliminary mechanistic study indicates that it is not very likely that both vinyl triflates and vinyl cations play major roles as intermediates in this transformation.
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Article Synopsis
- The research presents a nickel-catalyzed method for selectively attaching fluorinated heteroarenes to ketones, highlighting C-F bond activation.
- This process yields products with all-carbon quaternary stereocenters, achieving high efficiency with up to 99% yield and high enantiomeric excess (ee) values.
- The method also shows potential in drug development, as it can be applied to modify pharmaceuticals like donepezil in advanced stages.
Synthesis of 1-(1-Arylvinyl)pyridin-2(1)-ones from Ketones and 2-Fluoropyridine.
J Org Chem
October 2021
Department of Applied Chemistry, Yamaguchi University, Ube, Yamaguchi 755-8611, Japan.
We describe a simple and efficient procedure for the synthesis of -vinyl-substituted pyridones from ketones and 2-fluoropyridine in the presence of trifluoromethane sulfonic anhydride, followed by a base treatment. Various ketones with electron-donating or electron-withdrawing groups at the benzene rings can be used in this reaction. A preliminary mechanistic study indicates that it is not very likely that both vinyl triflates and vinyl cations play major roles as intermediates in this transformation.
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