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Divergent Fluorinations of Vinylcyclopropanes: Ring-Opening 1,5-Hydrofluorination and Ring-Retaining 1,2-Difluorination. 2023

Shuang Yang, and Jun-Yunzi Wu, and Shuang Lin, and Meicen Pu, and Zhi-Shu Huang, and Honggen Wang, and Qingjiang Li
Guangdong Provincial Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, 510006, P. R. China.

Organofluorine compounds have been widely used in pharmaceutical, agrochemical, and material sciences. Reported herein are divergent fluorination reactions of vinylcyclopropanes with different electrophiles, which allow the facile synthesis of homoallylic monofluorides and vicinal-difluorides through ring-opening 1,5-hydrofluorination and ring-retaining 1,2-difluorination, respectively. Both protocols feature mild conditions, simple operations, good functional group tolerance, and generally good yields. The practicality of these reactions is demonstrated by their scalability, as well as the successful conversion of the formed homoallylic monofluorides into other complex fluorinated molecules.

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