<p>Skeletal editing via nitrogen atom insertion into cyclic frameworks is a non-conventional and powerful strategy for constructing functionalized N heterocycles—privileged scaffolds in both synthetic chemistry and pharmaceutical science. Despite their importance, general methods for the direct insertion of nitrogen into carbocycles, particularly saturated ones, remain limited due to the challenge of selectively activating of inert C–C bonds. Here we report an electrochemical platform that enables efficient nitrogen atom insertion into saturated carbocycles under mild conditions. Two distinct protocols have been developed, allowing access to either functionalized quinolines or N-alkylated saturated N heterocycles, both with excellent selectivity and broad functional group tolerance. Mechanistic studies reveal the involvement of benzylic carbocation and cyclic imine intermediates, which undergo divergent pathways to furnish structurally diverse products. This methodology for N heterocycle synthesis provides a robust route to bioactive scaffolds. The synthetic utility of the approach is highlighted by the synthesis of two ion-channel antagonists.</p><p></p>