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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Efremova, N.V., Podryvanova, L.V., Vasil'eva, N.V. et al. Preparative Electrochemical Reduction of Fluorinated Benzonitriles. Russian Journal of Organic Chemistry 39, 212–218 (2003). https://doi.org/10.1023/A:1025588119221
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DOI: https://doi.org/10.1023/A:1025588119221