A Convenient Synthesis of Perfluoroalkylated and Fluorinated-Aryl Nitrogen Bases by Electrochemically Induced SRN1 Substitution

摘要: Indirect electrochemical reduction, by means of an aromatic anion mediator, perfluoroalkyl halides (CF3Br, n-C4F9I, n-C6F13I, I(CF2)4I) in the presence imidazole, 4(5)-nitroimidazole, 2-methyl-5-nitroimidazole, 2-(4‘-methoxyphenyl)imidazole, imidazole-2-carboxaldehyde, 4(5)-nitroimidazole-2-carboxaldehyde, 5(6)-nitrobenzimidazole, purines (adenine, hypoxanthine, xanthine, theophylline, lumazine) and pyrimidine anions (uracil, cytosine, barbituric acid) yields corresponding C-perfluoroalkylated nitrogen bases SRN1 mechanism. Aromatic nucleophilic substitution some fluorinated aryl 1-iodo-2-(trifluoromethyl)benzene 1-(4‘-iodo-tetrafluorophenyl)imidazole was also investigated it found that could react successfully under redox-catalyzed conditions with 2-(4‘-methoxyphenyl)imidazole anion, uracil to give 5-(fluorinated-aryl) bases. In case 1-(4‘-iodo-tetrafluorophenyl)imidazole, direc...