Single-Electron-Transfer-Induced C(sp3)-N Couplings via C-C Bond Cleavage of Cycloketoxime Esters

A practical single-electron-transfer-induced selective C(sp(3))-N coupling of cycloketoximes with anilines via C-C bond cleavage under copper-catalytic and synergetic photoredox/copper-catalytic reaction systems has been uncovered. These two powerful and simple protocols demonstrated excellent selectivity and good functional group compatibility without any base or ligand control. Preliminary mechanistic experiments indicated that a radical-mediated process was involved in these transformations.