Study On The Synthesis And Reactions Of Acyl Fluorides

Fluorine atom is located in the upper right corner of the periodic table of elements.It has the strongest electronegativity,which can offset the electron cloud distribution of molecules,thus affecting their physical and chemical properties.Introduction of fluorine atoms can often enhance the liposolubility,membrane penetration,metabolic stability,biological activity of the parent molecule.Thus,fluorine-containing compounds have been widely used in different fields.How to introduce fluorine atoms into molecules has been one of the key research fields in organofluorine chemistry.Based on Chen’s reagent（FSO₂CF₂COOMe）,we previously developed a new type of trifluoromethylation reagent—Cu（O₂CCF₂SO₂F）₂,which is an efficient nucleophilic trifluoromethylation reagent under mild conditions.This paper focuses on exploring its new use,and investigating the synthetic application of the perfluoalkyl acy fluorides.The thesis consists of the following two parts:（1）Cu（O₂CCF₂SO₂F）₂ was found to be a good deoxyfluorination reagent.It can efficiently and rapidly convert various carboxylic acids into the corresponding acyl fluorides.The reagent is a blue solid with good stability.It can be easily prepared in large scale from the reaction of fluorosulfonyl difluoroacetic acid and copper hydroxide.It is a good choice for rapid preparation of acyl fluorides from the corresponding carboxylic acids in laboratory.（2）In the presence of catalytic amounts of Cu I,perfluoroalkoxy anions generated in situ from perfluoroalkyl acyl fluorides and KF can react with various halogenated alkanes to efficiently produce the corresponding perfluoroalkoxylation products.In addition,the reaction can be carried out from easily available fluoroalkyl carboxylic acids by one-pot two-step method.