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Direct Photocatalytic Reductive Amidation of Nitroarenes: A Tandem Reduction–Decarboxylation Approach to Amide Bond Construction

Chenwei Liu, Xiaowen Qin, Weiheng Yuan, Heng Li, Shuhui Sun, Hongxia Li, Tiefeng Xu, Zhiping Yin

2025Organic Letters9 citationsDOI

Abstract

We report a photocatalytic strategy for direct amide synthesis from readily available nitroarenes and benzoylformic acids using flavin as an efficient photocatalyst. This one-pot transformation proceeds through a tandem reduction–decarboxylation–amidation sequence under mild blue light irradiation. Preliminary mechanistic studies indicated that nitrosoarene and N -hydroxyamides could be the key intermediates. The method demonstrates a broad substrate scope, excellent functional group tolerance, and remarkable operational simplicity, as it can be conducted under an ambient atmosphere. Notably, this protocol represents a significant advancement in step economy by directly employing diverse nitroarenes as nitrogen sources, avoiding the need for pre-reduced amine intermediates.

Topics & Concepts

ChemistryDecarboxylationTandemAmideReduction (mathematics)PhotocatalysisCombinatorial chemistryPeptide bondOrganic chemistryPhotochemistryCatalysisEnzymeMathematicsMaterials scienceGeometryComposite materialChemical Synthesis and AnalysisChemical Synthesis and ReactionsAsymmetric Hydrogenation and Catalysis