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Carbon–nitrogen transmutation in polycyclic arenol skeletons to access N-heteroarenes

Author

Listed:
  • Hong Lu

    (Northwest University)

  • Yu Zhang

    (Northwest University)

  • Xiu-Hong Wang

    (Northwest University)

  • Ran Zhang

    (Northwest University)

  • Peng-Fei Xu

    (Lanzhou University)

  • Hao Wei

    (Northwest University)

Abstract

Developing skeletal editing tools is not a trivial task, and realizing the corresponding single-atom transmutation in a ring system without altering the ring size is even more challenging. Here, we introduce a skeletal editing strategy that enables polycyclic arenols, a highly prevalent motif in bioactive molecules, to be readily converted into N-heteroarenes through carbon–nitrogen transmutation. The reaction features selective nitrogen insertion into the C–C bond of the arenol frameworks by azidative dearomatization and aryl migration, followed by ring-opening, and ring-closing (ANRORC) to achieve carbon-to-nitrogen transmutation in the aromatic framework of the arenol. Using widely available arenols as N-heteroarene precursors, this alternative approach allows the streamlined assembly of complex polycyclic heteroaromatics with broad functional group tolerance. Finally, pertinent transformations of the products, including synthesis complex biheteroarene skeletons, were conducted and exhibited significant potential in materials chemistry.

Suggested Citation

  • Hong Lu & Yu Zhang & Xiu-Hong Wang & Ran Zhang & Peng-Fei Xu & Hao Wei, 2024. "Carbon–nitrogen transmutation in polycyclic arenol skeletons to access N-heteroarenes," Nature Communications, Nature, vol. 15(1), pages 1-8, December.
  • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-48265-6
    DOI: 10.1038/s41467-024-48265-6
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    References listed on IDEAS

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    1. Hongyu Zhong & Dominic T. Egger & Valentina C. M. Gasser & Patrick Finkelstein & Loris Keim & Merlin Z. Seidel & Nils Trapp & Bill Morandi, 2023. "Skeletal metalation of lactams through a carbonyl-to-nickel-exchange logic," Nature Communications, Nature, vol. 14(1), pages 1-9, December.
    2. Shuai Liu & Xu Cheng, 2022. "Insertion of ammonia into alkenes to build aromatic N-heterocycles," Nature Communications, Nature, vol. 13(1), pages 1-8, December.
    3. Jisoo Woo & Colin Stein & Alec H. Christian & Mark D. Levin, 2023. "Carbon-to-nitrogen single-atom transmutation of azaarenes," Nature, Nature, vol. 623(7985), pages 77-82, November.
    4. Sean H. Kennedy & Balu D. Dherange & Kathleen J. Berger & Mark D. Levin, 2021. "Skeletal editing through direct nitrogen deletion of secondary amines," Nature, Nature, vol. 593(7858), pages 223-227, May.
    5. Jose B. Roque & Yusuke Kuroda & Lucas T. Göttemann & Richmond Sarpong, 2018. "Deconstructive diversification of cyclic amines," Nature, Nature, vol. 564(7735), pages 244-248, December.
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