The Conversion Of Functional Groups In α,α,α-iodo-difluoromethyl Ketones

Because of the metabolic stability and the characteristics of electronic absorption effect,difluoromethylene group（-CF₂-）often introduced into organic molecules,which can significantly change the molecular metabolic stability and bioavailability.Now,due to it widely used in the agrochemical,agrochemical and material fields,the development of difluoromethylene into the organic molecules has become one of the current hot research topic.We do some researches on the conversion of funcational groups inα,α,α-iododifluoromethyl ketones to enrich funcational difluoromethylation reagents,and expect to synthesize more complex containing difluoromethylene compounds effectively in this thesis.Firstly,the thesis pay attention to the selectively reduction on the carbonyl group inα,α,α-iododifluoromethyl ketones.We get 10 new difluoro building blocks via selective reduction reaction of iododifluoromethyl ketones substrates and NaBH₄.Also,we do some researches on the conversions of functional group ofα,α,α-iododifluoromethyl ketones with hydroxylamine or hydrazine hydrate.Secondly,we study the reaction that lithium triethylborohydride promotes the generation ofα,α-difluoroenolates fromα,α,α-iododifluoromethyl ketones to get self-condensation products,and applied to the synthesis of polyfluorinatedβ-hydroxy ketones via aldol reaction with aldehydes or ketones.The reaction indicates an unprecedented utilization of lithium triethylborohydride inα,α,α-iododifluoromethyl ketones and provide a new way to synthesisα,α-difluoroenolates.