Study On The Reaction Of Dibenzylzinc With Aromatic Aldehyde

Organozinc reagent is one of the earliest prepared organometallics. It is importantto form the C-C bonds. A variety of founctional groups may be tolerated in theseorganometallic reagents because of their moderate reactivity. Most importantly, thesereagent could react with a range of organic electrophiles under the presence of Lewisacid. Thus a large range of functional groups can be directly introduced into targetmolecules and possibly a shorter synthetic route would be realized by avoiding the useof protection-deprotection steps as well as functional group interconversions.Diorganozincs have found extensive application in asymmetric synthesis, sincethey add to aldehydes in the presence of a chiral catalyst with high enantioselectivity.However, the reactivity of diorganozincs are low in most cases, they react withaldehydes only after these reagents be transmetalated to corresponding organometallicreagents by CuCN or other transition metallic salts. Because few types of thedioraganozinc reagents limited to their further study .Alchols, stillbene, 2-diaryl ether and other kinds of compound can be sythesizedby the reaction of dibenzylzinc reagent with aromatic aldehyde. Expanded a newmethod to synthesis alkenyl, ether, alchol. In this thesis, 45 compounds all weresynthesized, among them, 32 products are new compounds.This thesis includes four chapters.Chapter One: Development of Polyfunctional Diorganozinc in OrganicSynthesisIn this section, a brief introduction of the development of polyfunctionaldiorganozinc in organic synthesis was given, and then reviewed in detail on thepreparation and reaction of polyfunctional diorganiczinc, which were of the mostimportance both on application and theory. At the same time, it showed that it wasdifficult to synthesis dibenzylzinc regant.Chapter Two: The Olefination Reaction of Polyfunctional dibenzylzinc with Aromatic AldehydeIn the absence of catalyst, the olefination can be synthesized by the reaction ofpolyfunction dibenzylzinc with aromatic aldehyde. The reactaion conditions wereoptimized. In this section, fifteen stilbenes and one 1,4-diphenyl-1,3-dibutadiene weresynthesized.Chapter There: The Reaction of Polyfunctional dibenzylzinc with AromaticAldehyde produced AlcholThis section seventeen compounds of 1,2-diaryl alcohol were synthesized. Thismethodology was proved to synthesis alcohol, especially 1,2-diaryl alchol.Chapter Four: The Reaction of Polyfunctional diorganozinc with AromaticAldehyde produced EtherTweleve compounds of 1,2-diaryl ether were synthesized in this section. Not onlyprovided a new method to synthesis 1,2-diaryl ether, but also enlarged the scopes ofthis reaction.