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

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.

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BibTeX

@misc{noel2026electrochemically,
  title = {{Electrochemically Hole-catalyzed Dearomative (3+2) Cycloaddition of Nitroarenes}},
  author = {Nathan Noël and Youssou Faye and Julien Legros and Laëtitia Chausset-Boissarie and Isabelle Chataigner},
  howpublished = {ChemRxiv},
  year = {2026},
  month = sep,
  doi = {10.26434/chemrxiv.15009160/v1},
  url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15009160/v1},
  note = {CC BY},
}

RIS

TY  - UNPB
TI  - Electrochemically Hole-catalyzed Dearomative (3+2) Cycloaddition of Nitroarenes
AU  - Nathan Noël
AU  - Youssou Faye
AU  - Julien Legros
AU  - Laëtitia Chausset-Boissarie
AU  - Isabelle Chataigner
PY  - 2026
DA  - 2026/09/21
PB  - ChemRxiv
DO  - 10.26434/chemrxiv.15009160/v1
UR  - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15009160/v1
AB  - 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.
ER  -

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