Enabling Access to 3-gem-Difluorovinyl Lactams via Zn-Mediated Sequential Single Electron Reductive Hydrodehalogenation
Jia Zheng
The Marine Biomedical Research Institute, School of Ocean and Tropical Medicine, Guangdong Medical University, Zhanjiang, Guangdong, 524023 China
The Marine Biomedical Research Institute of Guangdong Zhanjiang, Zhanjiang, Guangdong, 524023 China
Search for more papers by this authorXuran Liu
The Marine Biomedical Research Institute, School of Ocean and Tropical Medicine, Guangdong Medical University, Zhanjiang, Guangdong, 524023 China
Search for more papers by this authorJiawen Yin
The Marine Biomedical Research Institute, School of Ocean and Tropical Medicine, Guangdong Medical University, Zhanjiang, Guangdong, 524023 China
Search for more papers by this authorShuaikang Li
The Marine Biomedical Research Institute, School of Ocean and Tropical Medicine, Guangdong Medical University, Zhanjiang, Guangdong, 524023 China
Search for more papers by this authorJuanjuan Zhang
The Marine Biomedical Research Institute, School of Ocean and Tropical Medicine, Guangdong Medical University, Zhanjiang, Guangdong, 524023 China
Search for more papers by this authorCorresponding Author
Weigao Hu
The Marine Biomedical Research Institute, School of Ocean and Tropical Medicine, Guangdong Medical University, Zhanjiang, Guangdong, 524023 China
The Marine Biomedical Research Institute of Guangdong Zhanjiang, Zhanjiang, Guangdong, 524023 China
E-mail: [email protected]Search for more papers by this authorJia Zheng
The Marine Biomedical Research Institute, School of Ocean and Tropical Medicine, Guangdong Medical University, Zhanjiang, Guangdong, 524023 China
The Marine Biomedical Research Institute of Guangdong Zhanjiang, Zhanjiang, Guangdong, 524023 China
Search for more papers by this authorXuran Liu
The Marine Biomedical Research Institute, School of Ocean and Tropical Medicine, Guangdong Medical University, Zhanjiang, Guangdong, 524023 China
Search for more papers by this authorJiawen Yin
The Marine Biomedical Research Institute, School of Ocean and Tropical Medicine, Guangdong Medical University, Zhanjiang, Guangdong, 524023 China
Search for more papers by this authorShuaikang Li
The Marine Biomedical Research Institute, School of Ocean and Tropical Medicine, Guangdong Medical University, Zhanjiang, Guangdong, 524023 China
Search for more papers by this authorJuanjuan Zhang
The Marine Biomedical Research Institute, School of Ocean and Tropical Medicine, Guangdong Medical University, Zhanjiang, Guangdong, 524023 China
Search for more papers by this authorCorresponding Author
Weigao Hu
The Marine Biomedical Research Institute, School of Ocean and Tropical Medicine, Guangdong Medical University, Zhanjiang, Guangdong, 524023 China
The Marine Biomedical Research Institute of Guangdong Zhanjiang, Zhanjiang, Guangdong, 524023 China
E-mail: [email protected]Search for more papers by this authorComprehensive Summary
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 (D2O), 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.
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