Redox-Neutral Cross-Coupling Amination with Weak <i>N-</i>Nucleophiles: Arylation of Anilines, Sulfonamides, Sulfoximines, Carbamates, and Imines via Nickelaelectrocatalysis

A nickel-catalyzed cross-coupling amination with weak nitrogen nucleophiles is described. Aryl halides as well aryl tosylates can be efficiently coupled a series of N-nucleophiles, including anilines, sulfonamides, sulfoximines, carbamates, and imines via concerted paired electrolysis. Notably, electron-deficient anilines sulfonamides are also suitable substrates. Interestingly, when benzophenone imine applied in the arylation, product selectivity toward formation amine addressed by base switch. In addition, alternating current mode successfully applied. DFT calculations support facilitated reductive elimination pathway.