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  • Title: Regio-, stereo-, and enantioselective ipso- and migratory defluorinative olefin cross-coupling to access highly functionalized monofluoroalkenes.
    Author: Zeng D, Liu Z, Huang G, Wang Y, Zhu S.
    Journal: Nat Commun; 2024 Sep 02; 15(1):7645. PubMed ID: 39223147.
    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.
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