Dual Photoredox-/Palladium-Catalyzed Cross-Electrophile Couplings of Polyfluoroarenes with Aryl Halides and Triflates

A visible-light photoredox-/Pd-catalyzed cross-electrophile arylation of polyfluoroarenes with aryl halides and triflates in the presence of dialkylamines is reported for the first time. This synergistic protocol affords access to a series of fluorodiaryls from easily available starting materials under mild and operationally simple conditions. A series of mechanistic experiments, including the stoichiometric reactions of a ligated (aryl)Pd complex, Stern-Volmer fluorescence quenching studies, cyclic voltammetry studies, and UV-vis spectroscopy, were performed to elucidate the potential catalytic pathway in this synergistic process.

Automated summary

A visible-light photoredox-/Pd-catalyzed cross-electrophile arylation of polyfluoroarenes with aryl halides and triflates in the presence of dialkylamines has been reported for the first time. This synergistic protocol provides access to a series of fluorodiaryls from easily available starting materials under mild and operationally simple conditions. Mechanistic experiments, including stoichiometric reactions of a ligated (aryl)Pd complex, Stern-Volmer fluorescence quenching studies, cyclic voltammetry studies, and UV-vis spectroscopy, were performed to elucidate the potential catalytic pathway in this synergistic process.