NaH/Pd System For Michael Addition Reactions And Deallylation Reactions

This thesis includes two sections:The first section described a new method for reduction of electron-deficient alkenes mediated by palladium with sodium hydride.NaH is generally used as a base in organic synthesis.In sharp contrast,it is rarely used as a reductant.We demonstrate simply the addition of PdCl2 as a promotor switches the reactivity of a commonly used base NaH to a nucleophilic reductant.The reactivity is engineered into a Pd-mediated Michael addition reaction of sodium hydride to electron-deficient alkenes.This operationally simple and mild protocol displays a broad substrate scope and a broad spectrum of functional group tolerance.Moreover,the dual reactivity of NaH as a base and a reductant is demonstrated in cascade reactions.In the second section,we described a palladium-catalyzed reductive deallylation of aryl ethers and esters.This operationally simple,mild protocol affords products in high yield,and also displays a broad substrate scope and a broad spectrum of functional group tolerance and high chemoselectivity toward aryl ethers.In addition,this strategy can be used for the introduction of alkyl fragment at allyl position.