Triarylamines as catalytic donors in light-mediated electron donor–acceptor complexes
Durbis J. Castillo‐Pazos, Juan D. Lasso, Ehsan Hamzehpoor, Jorge Ramos-Sánchez, Jan Michael Salgado, Gonzalo Cosa, Dmitrii F. Perepichka, Chao‐Jun Li
Abstract
Recently, photochemistry of Electron Donor-Acceptor (EDA) complexes employing catalytic amounts of electron donors have become of interest as a new methodology in the catalysis field, allowing for decoupling of the electron transfer (ET) from the bond-forming event. However, examples of practical EDA systems in the catalytic regime remain scarce, and their mechanism is not yet well-understood. Herein, we report the discovery of an EDA complex between triarylamines and α-perfluorosulfonylpropiophenone reagents, catalyzing C-H perfluoroalkylation of arenes and heteroarenes under visible light irradiation in pH- and redox-neutral conditions. We elucidate the mechanism of this reaction using a detailed photophysical characterization of the EDA complex, the resulting triarylamine radical cation, and its turnover event.