Work

Electrochemically Hole-catalyzed Dearomative (3+2) Cycloaddition of Nitroarenes

Year: 2026

Type: preprint

Abstract: We report the first electrochemically hole-catalyzed (3+2) dearomative cycloaddition of nitroarenes, including benzene-based derivatives. Enabled by a hole-transfer chain process, the reaction proceeds through the anodic generation of a non-stabilized azomethine ylide from a readily available precursor, providing efficient access to structurally complex pyrrolidines from a broad range of electron-deficient nitroarenes. Remarkably, full conversion is achieved using catalytic amounts of electricity (0.1 F mol-1), resulting in high TONe (222) and Faradaic efficiency (925%). This work expands the scope of hole electrocatalysis beyond electron-rich olefins and establishes a new platform for electrochemical dearomative cycloadditions. The scalability of the method was further demonstrated under continuous-flow conditions.

Source: ChemRxiv

DOI: 10.26434/chemrxiv.15009160/v1

Authors: Nathan Noël, Youssou Faye, Julien Legros, Laëtitia Chausset-Boissarie, Isabelle Chataigner

Institutions: École Nationale Supérieure d'Ingénieurs de Caen, Laboratoire de recherche en cardiovasculaire, métabolisme, diabétologie et nutrition, Centre National de la Recherche Scientifique, Laboratoire de Chimie Théorique

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Indian National Science Academy, Agence Nationale de la Recherche, Centre National de la Recherche Scientifique, Université de Rouen, Normandie Université, Région Normandie

Awards: XLChem, Synthesizing our future, G1970702937, G2474904665, G2816262473, G2900821844, G2979748188, G4098071196, G4656594441, G5976147578, G7080048889, Synthèse Organique : des molécules au vivant, Reactivities of Electron-Deficient Arenes, G8864704675

OpenAlex ID: W7213891062

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