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Synthesis
DOI: 10.1055/a-2758-9872
Paper

A Photochemical Strategy for N-Aryl-ortho-Phenylenediamines Synthesis via Dearomative-Rearomative Coupling of Aryl Azides and Anilines

Authors

  • GIOVANNI VITTORIO AUGUSTO LENARDON 

    1   IOC, RWTH Aachen University, Aachen, Germany (Ringgold ID: RIN9165)

  • Xheila Yzeiri

    2   Institute of Organic Chemistry, RWTH Aachen University, Aachen, Germany (Ringgold ID: RIN9165)

  • Kristýna Kellovská

    2   Institute of Organic Chemistry, RWTH Aachen University, Aachen, Germany (Ringgold ID: RIN9165)

  • Esther Luisa Spaniol

    2   Institute of Organic Chemistry, RWTH Aachen University, Aachen, Germany (Ringgold ID: RIN9165)

  • Taisei Senzaki

    2   Institute of Organic Chemistry, RWTH Aachen University, Aachen, Germany (Ringgold ID: RIN9165)

  • Alessandro Ruffoni

    3   Institute of Organic Chemistry, Christian Albrecht Universitat zu Kiel, Kiel, Germany

  • Daniele Leonori

    2   Institute of Organic Chemistry, RWTH Aachen University, Aachen, Germany (Ringgold ID: RIN9165)
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This paper describes a novel strategy for the synthesis of N-aryl-ortho-phenylenediamines from aryl azides and anilines. The process employs low-energy photoexcitation to generate singlet nitrenes via decomposition of the aryl azide. The nitrene undergoes a dearomative N-insertion that, in the presence of a Lewis acid additive, enables aniline nucleophiles to be incorporated into the 3H-azepine product. Subsequent treatment with the electrophile Boc₂O triggers a 7-to-6 ring contraction that re-aromatizes the system to give N-aryl-ortho-phenylenediamines.



Publication History

Received: 13 October 2025

Accepted after revision: 28 November 2025

Accepted Manuscript online:
28 November 2025

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