Iodotrifluoromethylation Reaction Of Electron Deficient Olefin Derivatives

Trifluoromethyl as an important fluorine-containing group, the introduction of trifluoromethyl group into an organic molecule can often lead to a significant change of the precursor molecule on the physical, chemical and biological properties. Therefore, the development of efficient method for selective introduction of trifluoromethyl group into organic molecule has attracted much attention among organofluorine chemist. This thesis examined the iodotrifluoromethylation reaction of electron-deficient olefins with trifluoromethylated hypervalent iodine reagent.Firstly, phenyl acrylate was used as a substrate for the optimization of iodotrifluoromethylation condition, and iodotrifluoromethylated product can be obtained in65%isolated yield in the presence of zinc iodide (1.5equiv.) and trifluoromethyl-substituted hypervalent iodine reagent (1.5equiv.) after being refluxed for3h in chloroform. Then under this optimized condition, a series of acrylates, acrylonitrile, propenone, acrylamide derivatives can be iodotrifluoromethylated smoothly to afford the desired products in moderate to good yields. Finally, mechanistic studies suggested that the reaction experienced a radical course. The olefin iodotrifluoromethylation developed in this paper could avoid the use of gaseous trifluoroiodomethane, and has a potential value.