The New Method For Synthesis Of Arylacetamides By The Reaction Of Gem-Difluoroalkenes With DMF,and Primary And Secondary Amines

Amide group is an important unit and they have a wide appilication in natural compounds,medicines and pesticides.N,N-dimethylformamide(DMF)as a common chemical raw material and reagent has attracted great interests from chemists.Because the classic methods have some limitations in the synthesis of amides,therefore,the development of new and efficient methods for the synthesis of amide is highly desirable.With people's understanding,research and application of fluorine atom,the fluorine-containing compounds have a large proportion in organic synthesis,medicines and pesticides.As a consequence,they have attracted more and more attentions.gem-Difluoroalkenes were often used as the versatile fluorinated building blocks in organic synthesis to get different compounds through chemical transformation.In this dissertation,we developed a new method for the synthesis of arylacetamides by the reaction of various gem-difluoroalkenes with DMF,and primary and secondary amines,respectively.Highly efficient synthesis of novel amides are hot topic in organic synthesis.In the chapter 2,we successfully synthesized a variety of arylacetamides by the reaction of gem-difluoroalkenes with N,N-dimethylformamide(DMF)using KOtBu as base in the presence of water at 90 ? for 12 h under the metal-free condition.A series of arylacetamides were obtained in moderate to good yields.In addition,we also synthesized four novel 2-fluoro-2-aryloxyacetamide compounds by using this protocol.We proposed the possible mechanism of this reaction.Nineteen arylacetamides were synthesized in this chapter.In the chapter 3,we synthesized a variety of arylacetamides by the reaction of gem-difluoroalkenes with primary and secondary amines using KOtBu as base and DMSO as solvent in the presence of water at 90 ? for 12 h according to our previous reaction conditions.Twelve arylacetamides have been synthesized in moderate to high yields.The method exhibited wide substrate scope,high functional groups tolerance and operational simplicity.Therefore,it has potential applications in organic synthesis.In addition,tetrafluoroethylene generated in situ could also be converted to the corresponding difluoroacetamide under the optimized reaction conditions.