Chemical Transformation Of Compounds Containing Fluorosulfoxide

Organofluorine compounds show unique physical,chemical and biological properties in comparison with nonfluorinated parent compounds due to the introduction of fluorine atom.Thus,they have a very wide range of applications in pharmaceuticals,agrochemicals,and functional materials.Sulfoxides,as important medicine intermediates,have draw great research.However,fluorinated sulfoxides and their chemical transformation are rarely explored.In this thesis,we proceed different nucleophile reactions using aryl difluoromethyl sulfoxides,as follow:1)（arylsulfinyl）difluoromethylation reaction of alkyl halides using aryl sulfoxides（Ar SOCF₂H）and the corresponding functional group conversion;2)synthesis of arylsulfinyl difluoromethyl quaternary carbon center using alkyl bromide substituted phthalimide.The first part of this thesis is to study nucleophilic arylsulfonyl difluoromethylation of alkyl bromides and iodides with Ar SOCF₂H.The reaction has good substrate universality and is capable of obtaining aryl sulfinyl difluoromethylation products in32-92%yields for different carbon chain sizes of primary halogenated alkanes.This method has good functional group compatibility,including cyano,methoxy,tert-butyl,halogen and many other functional groups.In addition,the obtained aryl sulfinyl difluoromethylation products were chemically transformed to synthesize the corresponding compounds containing difluoromethyl,difluoroolefin,difluoromethyl phenyl sulfide,difluoromethylsilane,etc.Nevertheless,it was worth noting that the product of reacting difluoromethyl heteroaryl sulfoxides（2-Py SOCF₂H and BTSOCF₂H）with alkyl halides was not heteroaryl sulfoxides,but difluoroalkane sulfoxides.This thesis also investigated the successful construction of aryl sulfinyl difluoromethyl quaternary carbon-centered compounds containing aryl sulfinyl difluoromethyl sulfoxide by nucleophilic addition-substitution reactions using aryl difluoromethyl sulfoxide as a difluoroalkylation reagent.The reaction can successfully achieve the synthesis of aryl sulfinyl difluoromethyl quaternary carbon-centered compounds containing different ring sizes such as five,six and seven in 24-83%yields.In addition,the synthesis of different fluoroalkyl-substituted quaternary carbocenter compounds was examined comparatively,and the functional group conversion study of benzenesulfinyl difluoromethyl compounds was carried out.