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Photochemical rearrangement of isonitriles via energy transfer catalysis

Author

Listed:
  • Qi-Xin Dong

    (ShanghaiTech University
    ShanghaiTech University
    Nankai University)

  • Yi-Hong Ke

    (ShanghaiTech University)

  • Yi-Hui Tang

    (ShanghaiTech University)

  • Song Yu

    (The University of Manchester)

  • Huan-Ming Huang

    (ShanghaiTech University
    ShanghaiTech University
    Nankai University)

Abstract

Functional group interconversion, a pivotal synthetic technique for precise editing of molecular building blocks, is particularly rare when facilitated by energy transfer catalysis. Herein, we showcase two instances of photochemical rearrangement of isonitriles, facilitated by energy transfer catalysis under visible light. The di-π-ethane rearrangement and di-π-propane rearrangement proceed through a six-membered transition state, offering a fresh synthetic paradigm for constructing three- and five-membered molecular architectures. Notably, these open-shell rearrangements demonstrate a vast substrate scope, compatibility with diverse functional groups, and applicability to complex drug and natural product derivatives, thereby presenting a complementary strategy for advancing energy transfer-enabled functional group interconversion. Furthermore, the photochemical rearrangements of isonitriles have been supported by computational studies.

Suggested Citation

  • Qi-Xin Dong & Yi-Hong Ke & Yi-Hui Tang & Song Yu & Huan-Ming Huang, 2025. "Photochemical rearrangement of isonitriles via energy transfer catalysis," Nature Communications, Nature, vol. 16(1), pages 1-10, December.
  • Handle: RePEc:nat:natcom:v:16:y:2025:i:1:d:10.1038_s41467-025-64460-5
    DOI: 10.1038/s41467-025-64460-5
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    References listed on IDEAS

    as
    1. Ken Chen & Qingrui Zeng & Longhuan Xie & Zisheng Xue & Jianbo Wang & Yan Xu, 2023. "Functional-group translocation of cyano groups by reversible C–H sampling," Nature, Nature, vol. 620(7976), pages 1007-1012, August.
    2. Shu-Sheng Chen & Yu Zheng & Zhi-Xi Xing & Huan-Ming Huang, 2025. "Borylated strain rings synthesis via photorearrangements enabled by energy transfer catalysis," Nature Communications, Nature, vol. 16(1), pages 1-10, December.
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