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Electrochemical cascade access to hetero[8]circulenes as potent organophotocatalysts for diverse C–X bond formations

Author

Listed:
  • Ahmed S. Gabr

    (The University of Osaka)

  • Mohamed S. H. Salem

    (The University of Osaka
    Suez Canal University)

  • Md. Imrul Khalid

    (The University of Osaka
    Okinawa Institute of Science and Technology Graduate University)

  • Ryota Takahashi

    (The University of Osaka)

  • Yoshihiro Nishimoto

    (The University of Osaka)

  • Makoto Yasuda

    (The University of Osaka)

  • Shinobu Takizawa

    (The University of Osaka)

Abstract

The chemistry of hetero[8]circulenes has been limited to three main types, constrained by synthetic challenges in creating unsymmetrical variants. Herein, we introduce an electrochemical approach to a type of hetero[8]circulene, featuring five hexagons and three pentagons. Our method capitalizes on the sustainability and selectivity of electrochemistry, utilizing differential oxidation potentials to generate dioxaza[8]circulenes through selective intermolecular and intramolecular couplings under mild conditions, achieving yields of up to 83% with good functional group tolerance. We further refine this process into a one-pot protocol using commercially available substrates, forming six new bonds. Comprehensive structural, optical, and electrochemical characterizations, including X-ray crystallography, spectrophotometric analysis, and DFT calculations, are conducted. Inspired by their distinct structural and redox properties, we explore the application of dioxaza[8]circulenes as organophotocatalysts for diverse C–X (X = C, B, S, P) bond formation achieving up to 97% yields under LED light irradiation (365 nm) without transition metals.

Suggested Citation

  • Ahmed S. Gabr & Mohamed S. H. Salem & Md. Imrul Khalid & Ryota Takahashi & Yoshihiro Nishimoto & Makoto Yasuda & Shinobu Takizawa, 2025. "Electrochemical cascade access to hetero[8]circulenes as potent organophotocatalysts for diverse C–X bond formations," Nature Communications, Nature, vol. 16(1), pages 1-12, December.
    • Handle: RePEc:nat:natcom:v:16:y:2025:i:1:d:10.1038_s41467-025-60889-w
    DOI: 10.1038/s41467-025-60889-w
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