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Updated: Jun 10, 2026

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Published on: May 26, 2019
Nickel-Catalyzed 6-endo-trig Reductive Heck Cyclization of Vinyl Fluorides to Access 3-Fluorinated
Juanjuan Zhang1, Tangji Chen1, Yingyu Yang1
1School of Ocean and Tropical Medicine, Guangdong Medical University, Zhanjiang, Guangdong 524023, P. R. China.
Abstract:
Intramolecular carbometalation-based difunctionalizations of alkenes have been well-developed. In most of the processes, the 5-exo-trig cyclization is highly favored over the 6-endo-trig carbometalation. Furthermore, fluorinated alkenes are still unexplored in these reactions due to the β-F elimination of the alkyl metal species. Herein, we report a dual ligand catalytic system for the 6-endo-trig reductive Heck reaction, which might undergo nickel-based dyotropic rearrangement. This methodology allowed rapid synthesis of 3-F-dihydroquinolinones, showing good tolerance of functionality and compatibility of various bioactive skeletons. This reaction expands the α substituents of alkenes from alkyl/aryl groups to challenging fluoride, which also opens up a new possibility for the intramolecular difunctionalizations of vinyl fluoride.
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