Electrochemical Single-Carbon Insertion via Distonic Radical Cation Intermediates.

ABSTRACT: The synthesis of polysubstituted (hetero)aromatic compounds is essential in various fields, including pharmaceuticals, where such compounds are fundamental to many approved drugs. In this study, we present a novel electrochemical method for single-carbon insertion targeting various (hetero)aromatic compounds, with a particular focus on pyridines. In this process, the electrochemical oxidation of pyrrole derivatives produces a radical cation intermediate, which then undergoes nucleophilic attack by diazo compounds to yield polysubstituted pyridine derivatives. Notably, the insertion position is influenced by the electronic properties of N-protecting groups, allowing for unprecedented para-selective insertion through the introduction of electron-withdrawing groups. Insights fro

SUBMITTER: Morimoto T 

PROVIDER: S-EPMC12291465 | biostudies-literature | 2025 Jul

REPOSITORIES: biostudies-literature