Enabling Access to 3-gem-Difluorovinyl Lactams via Zn-Mediated Sequential Single Electron Reductive Hydrodehalogenation

Jia Zheng; Xuran Liu; Jiawen Yin; Shuaikang Li; Juanjuan Zhang; Weigao Hu

doi:10.1002/cjoc.202400718

Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (3) : 255 -260. DOI: 10.1002/cjoc.202400718

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Enabling Access to 3-gem-Difluorovinyl Lactams via Zn-Mediated Sequential Single Electron Reductive Hydrodehalogenation

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Abstract

Herein, we describe a direct route for the synthesis of 3- gem-difluorovinyl lactams through Zn-mediated reductive hydrodehalogenation. Importantly, by using inexpensive deuterium oxide (D ₂O), the high value-added vicinal dideuterated gem-difluoroalkenes with excellent deuterium (D) incorporation were prepared. Mechanism studies indicated a successive single electron transfer process: the reaction initially undergoes hydrodechlorination to give the intermediate α-trifluoromethylidene lactams, which are then activated by the in-situ generated zinc cations and reduced to the desired product via hydrodefluorination.

Keywords

3- gem-Difluorovinyl lactams / Dideuterium compounds / Zn-mediated / Single electron reduction / Hydrodehalogenation / Radicals / Lewis acidity / Zinc cation

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Jia Zheng, Xuran Liu, Jiawen Yin, Shuaikang Li, Juanjuan Zhang, Weigao Hu. Enabling Access to 3-gem-Difluorovinyl Lactams via Zn-Mediated Sequential Single Electron Reductive Hydrodehalogenation. Chinese Journal of Chemistry, 2025, 43(3): 255-260 DOI:10.1002/cjoc.202400718