Preparative Electrochemical Reduction of Fluorinated Benzonitriles.

Abstract

Electrolysis Electrolysis M 4000Preparative Electrochemical Reduction of Fluorinated Benzonitriles. -Electrochemical reduction of fluorinated benzonitriles like (I) in aprotic media is accompanied by the competing processes of fragmentation to (II) and dimerization to (III). The ratio of both processes is influenced by the use of a mediator such as anthracene or 4-cyanopyridine. The electrochemical reduction of the fluorinated benzonitrile (IV) in the presence of tetrabutylammonium thiophenolate and a mediator leads via S RN 1 nucleophilic fluorine substitution to (VI). -(EFREMOVA, N. V.; PODRY-VANOVA, L. V.; VASIL'EVA, N. V.; STARICHENKO, V. F.; SHTEINGARTS, V. D.; Russ.

Radical Anions of Aromatic Carbonitriles as Reagents for Arylation of Fluorinated Benzonitriles

“…Dicyanobiphenyls can arise as a result of the ET from 3 •− to fluorobenzonitriles 4 to afford radical anions prone to dimerization followed by the departure of fluoride. 31,32 Scheme 3 illustrates the reaction pathway proposed for the phenylation of fluorinated benzonitriles 4 by radical anion 3 •− with trifluorobenzonitrile 4e. At the first stage, the substitution of the o-and p-fluorine atom in benzonitrile 4e by the 3 •− ipsocarbon atom bearing the maximum electron density (see Figure 1) takes place, leading to the corresponding biphenyl radicals 8 ortho and 8 para .…”