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An unexpected synthesis of azepinone derivatives through a metal-free photochemical cascade reaction

Author

Listed:
  • Lina Song

    (Heidelberg University)

  • Xianhai Tian

    (Heidelberg University)

  • Kaveh Farshadfar

    (Islamic Azad University, Central Tehran Branch, Poonak
    Aalto University)

  • Farshad Shiri

    (Islamic Azad University, Central Tehran Branch, Poonak)

  • Frank Rominger

    (Heidelberg University)

  • Alireza Ariafard

    (Islamic Azad University, Central Tehran Branch, Poonak
    University of Tasmania)

  • A. Stephen K. Hashmi

    (Heidelberg University
    King Abdulaziz University)

Abstract

Azepinone derivatives are privileged in organic synthesis and pharmaceuticals. Synthetic approaches to these frameworks are limited to complex substrates, strong bases, high power UV light or noble metal catalysis. We herein report a mild synthesis of azepinone derivatives by a photochemical generation of 2-aryloxyaryl nitrene, [2 + 1] annulation, ring expansion/water addition cascade reaction without using any metal catalyst. Among the different nitrene precursors tested, 2-aryloxyaryl azides performed best under blue light irradiation and Brønsted acid catalysis. The reaction scope is broad and the obtained products underwent divergent transformations to afford other related compounds. A computational study suggests a pathway involving a step-wise aziridine formation, followed by a ring-expansion to the seven-membered heterocycle. Finally, water is added in a regio-selective manner, this is accelerated by the added TsOH.

Suggested Citation

  • Lina Song & Xianhai Tian & Kaveh Farshadfar & Farshad Shiri & Frank Rominger & Alireza Ariafard & A. Stephen K. Hashmi, 2023. "An unexpected synthesis of azepinone derivatives through a metal-free photochemical cascade reaction," Nature Communications, Nature, vol. 14(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:14:y:2023:i:1:d:10.1038_s41467-023-36190-z
    DOI: 10.1038/s41467-023-36190-z
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