Preparation of biologically relevant 3-hydroxyisoindolinones from readily available 2-alkynylbenzamides is an appealing synthetic approach. However, such kinds of compounds preferably undergo O-attacked 5-exo-dig/6-endo-dig cyclizations. Herein, we report an electrochemically generated amidyl radical proceeding via a highly selective N-attacked 5-exo-dig radical cyclization to form 3-hydroxyisoindolinone derivatives. This reaction features simple operation, good selectivity, and broad substrate scope. Moreover, gram-scale preparation and synthetic elaborations imply the potential applicability of this protocol for the synthesis of diverse isoindolinone derivatives.