Preparative Electrochemical Reduction of Fluorinated Benzonitriles |
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Authors: | Efremova N. V. Podryvanova L. V. Vasil'eva N. V. Starichenko V. F. Shteingarts V. D. |
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Affiliation: | (1) Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Division, Russian Academy of Sciences, Novosibirsk, 630090, Russia |
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Abstract: | Electrochemical reduction of fluorinated benzonitriles in aprotic media is accompanied by concurrent processes of dimerization and fragmentation of the corresponding anion-radicals. With 2-fluoro- and 3,4,5-trifluorobenzonitriles the defluorinated products can be obtained at direct electrochemical reduction; for the other compounds studied have been found mediators providing a possibility to obtain in high yield defluorinated products at preparative electrochemical reduction. A fundamental possibility was demonstrated of providing products by nucleophilic fluorine substitution by SBN mechanism at electrochemical reduction of fluorinated benzonitriles in aprotic solvents in the presence of mediators. |
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