Studies On New Strategies Exploration For Synthesis Of Organofluoride And Organophosphine Compounds

Organofluorine and organophosphine compounds are widely used in medicinal chemistry and materials science due to their unique chemical properties and biological activities.Therefore,the development of simple and effective strategies to synthesize multifunctional organofluorine and organophosphine compounds has attracted much attention.This dissertation separately summarizes the synthesis methods of these two types of compounds and describes the four highly functional organofluorine and organophosphine compounds synthesized by this method in detail.This dissertation includes the following five parts:1.The synthesis methods of organofluorine and organophosphine compounds were classified and summarized.The content mainly focuses on the construction of organic carbon-fluorine bonds and carbon-phosphine bonds and building block synthesis methods containing fluorine and phosphine synthons.2.The reaction of oxyfluorination of olefins for the synthesis of?-fluoroketones was studied in detail.In this reaction,without the participation of metals,Selectfluor^TM was used as the fluorine source,and the C-F bond construction and Wacker oxidation reaction were completed in one step by using the olefin difunctionalization strategy,and the?-fluoroketones were efficiently synthesized.Preliminary mechanism investigations indicated that the reaction might involve a radical process.3.Thereactionofphotoredox-catalyzedintermolecular amino-difluoromethylphosphonylation of alkenes was studied in detail.In this reaction,a new type of photoredox catalysis is adopted,and bromodifluoromethyl phosphate was used as a difluoro reagent to efficiently synthesize?,?-difluoro-?-aminophosphonates by using anolefindifunctionalizationstrategyandderivatizationtoobtain?,?-difluoro-?-Aminophosphoric acid.4.The reaction of palladium-catalyzed migratory insertion of isocyanides for synthesis of C?phosphonoketenimines was studied in detail.Preliminary mechanistic investigations revealed that the Pd?0?active species first intercalated into the isocyanides,followed by the oxidative addition of the phosphonated halides,and finally the?-H reduction eliminated to afford C-phosphonoketenimines.5.The reaction of Pd-catalyzed AQ directed C?sp³?-H alkylation to construct chiral??phosphono-?-amino acids was studied in detail.The reaction was able to synthesize a series of important?-phosphono-?-amino acids with high regioselectivity and stereoselectivity and derivatized to obtain two biological inhibitors,L-AP4 and L-phosphinothricin.