Formal Hydrosilylation Of Olefins And Dehalogenative Deuteration Of Aryl Halides Involving Silyl Anions

As an important part of organosilicon chemistry,the reactions involving silyl anions play a significant role in organic synthesis,drug development,and material sciences.Silyl anion-mediated reactions have been extensively studied and considerable progress has been made in the past few decades.This thesis describes our effors to develop novel reactions of silyl anion generated by disilane and nuclephiles such as potassium methoxide and cesium fluoride which is divided into two secions1.A cesium fluoride-mediated formal hydrosilylation of olefins was developed using hexamethyldisilane as the silane source.In this research protocol,hexamethyldisilane is used to replace the flammable and explosive trimethylsilane,which provides a new method for the preparation of trimethylsilyl compounds.In addition,when deuterated solvent is used,?-deuterated organosilanes were obtained(chapter 2).2.A general KOMe/disilane-mediated ipsodehalogenative deuteration reaction was developed with CD₃CN as solvent/deuterium source.This method features operationally simple procedure,mild reaction conditions,readily available reagents,and good functional group tolerance.A diverse range of valuable deuterated(hetero)arenes,natural products,and pharmaceuticals were isotopically labeled with excellent deuterium incorporation and specificity.Moreover,a brief investigation of the mechanism was carried out experimentally and coumputationally(chapter 3).