Ge Chenxin, Wang Bin, Jiang Yunchen, Chen Chao
Key Laboratory of Bioorganic Phosphorus & Chemical Biology (Ministry of Education, MOE), Tsinghua University, 100084, Beijing, China.
State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin, 300071, China.
Commun Chem. 2022 Dec 3;5(1):167. doi: 10.1038/s42004-022-00772-7.
The synthesis of gem-difluoroethylene compounds remains a difficult task in organic synthesis. Here, the direct difluoroethylation reactions of N- and O-nucleophiles including amides and acids were realized with a hypervalent iodine reagent: gem-difluorovinyl iodonium salt (DFVI). The reactions were accomplished via a neighbouring group rearrangement. The gem-difluorovinyl iodonium salt was found to display diverse reactivity due to its unique electronic effect and was applied to the incorporation of difluoroethylene group, including difluorovinylation of carboxylic acids, difluorovinylation and 1,3-cyclic fluorovinylation of amides and 1,1-cyclic difluoroethylation of amines.
偕二氟乙烯化合物的合成在有机合成中仍然是一项艰巨的任务。在此，利用高价碘试剂：偕二氟乙烯基碘鎓盐（DFVI）实现了包括酰胺和酸在内的N-和O-亲核试剂的直接二氟乙基化反应。这些反应通过邻基重排完成。发现偕二氟乙烯基碘鎓盐由于其独特的电子效应而表现出多样的反应性，并被应用于偕二氟乙烯基的引入，包括羧酸的二氟乙烯基化、酰胺的二氟乙烯基化和1,3-环氟乙烯基化以及胺的1,1-环二氟乙基化。
Zotero 插件
