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

Daning Zeng, Zihao Liu, Guoce Huang, You Wang () and Shaolin Zhu ()
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Daning Zeng: Nanjing University
Zihao Liu: Nanjing University
Guoce Huang: Nanjing University
You Wang: Nanjing University
Shaolin Zhu: Nanjing University

Nature Communications, 2024, vol. 15, issue 1, 1-9

Abstract: 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.

Date: 2024
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DOI: 10.1038/s41467-024-52054-6

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