Synthesis Of Aryl Tertiary Amines And Tert-alkyl-containing Gem-Difluoroolefins

The incorporation of fluorine-containing groups into organic molecules often drastically alters the chemical,physical and biological properties of the parent compounds.Therefore,organofluorine compounds are receiving increasing attention from synthetic and medicinal chemistry communities.But with the development of fluorine chemistry and fluorine industry,more and more fluorinated compounds have been produced in our daily life and contaminated our environment.Carbon-fluorine(C-F)bonds are generally considered to be difficult to be cleaved because of their high bond energy.The cleavage of C-F bond with simple and efficient method is a great challenge for organic chemists.In this thesis,we focused on the cleavage of C-F bond and studied the amination of fluoroarenes and the coupling reaction of a-trifluoromethyl-styrene with tert-Grignard reagent.In the second chapter,we have developed an amination reaction of fluoroarenes with secondary amines via benzyne intermediates in the presence of nBuLi.A variety of versatile aryl tertiary amine compounds were obtained.In the third chapter,we have described a facile method for the synthesis of t-butyl-containing gem-difluoroalkenes by the reaction of ?-trifluoromethyl-styrene with tert-Grignard reagent via the classical SN2' reaction in the presence of CuCN.