Regio-, stereo-, and enantioselective ipso- and migratory defluorinative olefin cross-coupling to access highly functionalized monofluoroalkenes.
basic_science · Level V
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- Record sourced from PubMed, PMID 39223147.
- Also identified by DOI 10.1038/s41467-024-52054-6 and PMC identifier 11368934.
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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(sp<sup>3</sup>)-H/C(sp<sup>2</sup>)-F activation with high levels of regio-, stereo-, and enantiocontrol.