Copper-Catalyzed Perfluoroalkylation Of Alkynes And Mn^Ⅲ-Mediated Synthesis Of β-Fluorinated Alkylphosphonates

Organofluorine compounds have received extensive attention in recent decades,because the incorporation of perfluoroalkyl groups or fluorine atoms into the organic molecules could enhance polarity,lipophilicity,chemical and metabolic stability of the compound.It is widely used in medicine,pesticides,materials and other fields.At present,the synthesis of perfluoroalkyl compounds is still limited.It is particularly important to develop perfluoroalkane synthesis methods with mild conditions,wide substrate applicability,and high functional group compatibility.This thesis consists of two parts:Part I:Copper-catalyzed perfluoroalkylation of alkynesAn efficient and comprehensive method for copper-catalyzed cross-coupling reaction of alkynyl bromides was successfully developed.This method proceeds under mild reaction conditions with high efficiency and shows a widely functional compatibility,providing a series of fluoroalkylated alkynes in good yields.One-pot synthesis simplifies the experimental operation.In addition,the reasonable reaction mechanism was discussed in this chapter.Part 2:Mn^Ⅲ-mediated synthesis ofβ-fluorinated alkylphosphonatesThe reaction of phosphonofluorination of alkene mediated by manganese salt was successfully developed.The condensation of various alkenes with diethyl phosphate and selectfluor in DMF led to synthesis ofβ-fluorinated alkylphosphonates.This reaction has the advantages of mild conditions（60℃）,excellent yield,and good substrate applicability.