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Cyano group translocation to alkenyl C(sp2)–H site by radical cation catalysis

Author

Listed:
  • Luyang Li

    (Southeast University)

  • Tongyan Yu

    (Southeast University)

  • Kemeng Du

    (Southeast University)

  • Pan Xu

    (Southeast University)

Abstract

Achieving the direct translocation of a functional group to unactivated C–H sites within a molecule, while maintaining its structural integrity, presents a notable challenge in the realm of organic synthesis. Here, we report that photocatalytic quinuclidine-based radical cation catalysis can enable selective 1,4-cyano translocation to alkenyl C(sp2)–H sites without imparting any extraneous modifications. The approach leverages N-centered radical cations as catalysts to facilitate both radical translocation and ionic elimination, thereby restoring the double bond and enabling positional exchange between a CN group and a C(sp2)–H bond. This results in the formation of alkenyl cyanide, a versatile linchpin that can easily undergo substitution reactions with a wide range of nucleophiles then lead to diverse difunctionalizations of alkenes. Consequently, this CN translocation approach complements the existing state-of-the-art method of radical-induced alkene 1,2-difunctionalization via functional group translocation.

Suggested Citation

  • Luyang Li & Tongyan Yu & Kemeng Du & Pan Xu, 2025. "Cyano group translocation to alkenyl C(sp2)–H site by radical cation catalysis," Nature Communications, Nature, vol. 16(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:16:y:2025:i:1:d:10.1038_s41467-025-62585-1
    DOI: 10.1038/s41467-025-62585-1
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    References listed on IDEAS

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    1. Marvin Mendel & Teresa M. Karl & Jegor Hamm & Sherif J. Kaldas & Theresa Sperger & Bhaskar Mondal & Franziska Schoenebeck, 2024. "Dynamic stereomutation of vinylcyclopropanes with metalloradicals," Nature, Nature, vol. 631(8019), pages 80-86, July.
    2. 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.
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