Studies On Metal-Free Reduction Of Alkynones And Conversion Of Trifluoromethylated Alcohol Compounds

This paper reviewed the research progress of defunctionalization of carbonyl compounds.The 1,2-selective reduction of alkynones catalyzed by B（C₆F₅）₃ was studied.In addition,the metal-free nucleophilic substitution ofα-CF₃ allylic alcohols/propargylic alcohols was also studied.This paper was divided into three chapters.Chapter 1 Progress in defunctionalization of carbonyl compounds（review）.In this chapter,we briefly reviewed the research progress of defunctionalization of carbonyl compounds.This review was organized according to the reaction conditions and reaction types.Chapter 2 The 1,2-selective reduction of alkynones catalyzed by B（C₆F₅）₃.In this chapter,we have developed an organoborane-catalyzed selective 1,2-reduction reaction of alkynones for the synthesis of benzyl alkyne compounds.This transformation displays many advantages including transition metal-free,mild reaction conditions,low catalyst loading（5 mol%）,high yield（up to 99%）,broad substrate scope and functional group tolerance.In addition,benzyl alkyne products can be converted into other useful chemical compounds.This method provides an expedient way to the synthesis of benzyl alkynes.Chapter 3 Study on metal-free nucleophilic substitution ofα-CF₃ allylic alcohols/propargylic alcohols.In this chapter,we mainly developed a method to reactα-CF₃ allylic alcohols/propargylic alcohols with nucleophile to produce the corresponding trifluoromethylated products using TMSCl as the hydroxyl protective group and becoming the leaving group in a mixed solvent DCM:HFIP or HFIP.This method has many advantages including metal-free,mild reaction conditions and wide range of substrates.