Direct C–H photoarylation of diazines using aryldiazonium salts and visible-light

In this study, direct C–H photoarylation of pyrazine with aryldiazonium salts under visible-light irradiation (blue-LEDs) is described, and additional examples including photoarylations of pyrimidine and pyridazine are also covered. The corresponding aryl-diazines were prepared in yields up to 84% only by mixing and irradiating the reaction with no need for an additional photocatalyst. We demonstrate the efficacy of this protocol by the scope with electron-donor, -neutral, and -withdrawing groups attached at the ortho, meta, and para positions of the aryldiazonium salts; the results are better than those reported for ruthenium-complex mediated photoarylations. Additionally, we demonstrate the robustness of this methodology with a 5 mmol scaled-up experiment. Mechanistic studies were carried out giving support to the proposal of a photocatalyzed approach by an electron donor–acceptor (EDA) complex, also highlighting the crucial role that solvents play in the formation of the EDA complex.

An electron donor–acceptor (EDA) approach for the direct C–H photoarylation of diazines using aryldiazonium salts and visible-light is described.