Transition metal-free electrochemical fluorotrifluoromethylation of Styrenes

An environmentally friendly electrochemical fluorotrifluoromethylation of styrenes was developed via the tandem processes of electro-oxidation and radical and nucleophilic addition. By using commercial CF3SO2Na and Et3N center dot 3HF as the CF3 and F sources, respectively, a series of potentially bio-active multi-site F-containing compounds were obtained in moderate to good yields. This fluorotrifluoromethylation strategy is catalyst- and oxidant-free, and demonstrates mild conditions and high step economy features. In addition, several analytical methods, including cyclic voltammetry and control experiments, were conducted to investigate a reasonable reaction mechanism.

Automated summary

An environmentally friendly electrochemical fluorotrifluoromethylation of styrenes was developed, which involves tandem processes of electro-oxidation and radical and nucleophilic addition. Using commercial CF3SO2Na and Et3N•3HF as the sources of CF3 and F, a range of potentially bio-active multi-site F-containing compounds were obtained in moderate to good yields. This catalyst- and oxidant-free fluorotrifluoromethylation strategy offers mild conditions and high step economy features, and the reaction mechanism was investigated using several analytical methods.