Electrooxidation-Induced C(sp3)-H/C(sp2)-H Radical-Radical Cross-Coupling between Xanthanes and Electron-Rich Arenes

Comprehensive Summary The arylation of C(sp(3)) - H bonds has been a priority research topic in organic synthesis. Minsici reactions have been the powerful methods for C(sp(3)) - C(sp(2)) bonds formation. Despite its mature development, the scopes of arenes are usually suitable for electron-deficient heterocyclic compounds, rather than electron-rich arenes. Herein, we report an electrooxidation-induced alkylation of electron-rich arenes with H-2 evolution under exogenous oxidant-free conditions, avoiding the utilization of metal catalysts. This protocol is well performed with various electron-rich aniline derivatives and nitrogen-containing heterocyclic compounds. We anticipate that this electro-oxidative C(sp(3)) - H arylation represents an important expansion for the classic arenes alkylation, thereby proving an attractive strategy for the developments of radical cross-coupling chemistry.