Photoinduced Phenolate Organocatalysis for Isoindoloindolone Synthesis with N-Iodobenzoyl Indoles

An efficient photoinduced phenolate organocatalytic methodology for the synthesis of isoindoloindolones was developed, demonstrating a broad substrate scope with high yields and excellent functional group tolerance. Mechanistic studies confirmed a direct single-electron transfer pathway facilitated by an excited phenolate catalyst to N-iodobenzoyl indoles, validated through UV–vis spectroscopy, fluorescence quenching, and cyclic voltammetry. This approach enables the synthesis of biologically significant derivatives including melatonin MT₃ and 5-HT₆ receptor ligands.