Application Of PhIClCF₃ In Trifluoromethylation Of Electron-Rich Arenes

Trifluoromethyl compounds account for a very large proportion in organic fluorides and play a pivotal role in many fields such as medicine,materials electronics.Trifluoromethylation reagents is closely relate to development of trifluoromethylation reaction.The cyclic phenyl trifluoromethyl hypervalent iodine reagent prepared by Togni's group is the simplest form of electrophilic trifluoromethyl reagents.Although it has beenwidely used,the problems of high cost,difficult to synthesize,and activation remain to be addressed.In 2016,the acyclic trifluoromethyl hypervalent iodine reagent PhICF₃Cl developed by our group solved these problems.PhICF₃Cl with external coordination structure,Since it is ionic,it has a more efficient CF₃ transfer ability than the covalent Togni reagent.This reagent has many advantage such as low cost,easy to synthesize,stable at normal temperature,and strong reaction activity.It provides a breakthrough basis for the synthesis and application of ArICF₃X.This thesis studied the directtrifluoromethylation of electronricharomatics by PhICF₃Cl reagent,In this paper,the direct trifluoromethylation of PhICF₃Cl with electron-rich aromatic hydrocarbons was studied under solvent and solvent-free conditions.The details are given below:1.Introduction:?1?Overview of trifluoromethylation reaction and various trifluoromethylation reagents;It mainly clarifies the development history,preparation method and application range of two electrophilic trifluoromethylation reagents,Umemoto reagent and Togni reagent.?2?Development history of arenes trifluoromethylation and heteroaromatic ring trifluoromethylation.2.The significance of the topic selection:On the basis of the application of trifluoromethyl high-valent iodine reagent and the development of trifluoromethylation of electron-rich arenes.Selecting an electron-rich arenes as a soft nucleophile and using a PhICF₃Cl reagent for catalyst-free trifluoromethylation of electron-rich arenes,enriching the method of electrophilic trifluoromethylation.To provide trifluoromethyl-containing electron-rich aromatic and heteroaromatic compounds with physicochemical properties for materials,biology and other fields.3.This paper showed that is possible to realize the direct trifluoromethylation of aromatic,halogenated aromatic and indole without additives using our reagent.Twenty aromatic containing trifluoromethyl were synthesized in both solvent and solvent-free conditions.And they were marked with ¹H NMR,¹⁹F NMR,¹³C NMR and MS.Thus,a green trifluoromethylation method for electronic aromatics has been established.