Work

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

Year: 2024

Type: article

Abstract: Comprehensive 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.

Source: Chinese Journal of Chemistry

DOI: 10.1002/cjoc.202400718

Authors: Jia Zheng, Xuran Liu, Jiawen Yin, Shuaikang Li, Juanjuan Zhang, Weigao Hu

Institution: Guangdong Medical College

Language: English

Topic: Fluorine in Organic Chemistry

Subfield: Pharmaceutical Science

Field: Pharmacology, Toxicology and Pharmaceutics

Domain: Life Sciences

Open Access status: bronze

Funder: Basic and Applied Basic Research Foundation of Guangdong Province

Award: G7082951386