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Regio-, stereo-, and enantioselective ipso- and migratory defluorinative olefin cross-coupling to access highly functionalized monofluoroalkenes

Author

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  • Daning Zeng

    (Nanjing University)

  • Zihao Liu

    (Nanjing University)

  • Guoce Huang

    (Nanjing University)

  • You Wang

    (Nanjing University)

  • Shaolin Zhu

    (Nanjing University
    Henan Normal University
    Shanghai Jiao Tong University)

Abstract

Monofluoroalkenes serve as nonhydrolyzable mimetics of amides and are frequently encountered in drug candidates. Herein we report a regio-, enantio-, and stereoselective NiH-catalyzed ipso- and migratory defluorinative olefin cross-coupling employing readily available olefins and gem-difluoroalkenes under mild conditions. This approach enables the efficient synthesis of a broad array of structurally diverse monofluoroalkenes bearing a tertiary allylic stereogenic center. Mechanistically, the challenging migratory defluorinative olefin cross-coupling process is successfully realized through a ligand relay catalytic strategy, enabling the formal C(sp3)–H/C(sp2)–F activation with high levels of regio-, stereo-, and enantiocontrol.

Suggested Citation

  • Daning Zeng & Zihao Liu & Guoce Huang & You Wang & Shaolin Zhu, 2024. "Regio-, stereo-, and enantioselective ipso- and migratory defluorinative olefin cross-coupling to access highly functionalized monofluoroalkenes," Nature Communications, Nature, vol. 15(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-52054-6
    DOI: 10.1038/s41467-024-52054-6
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