NaBARF-catalyzed Intermolecular Oxidative Cyclization Of Dialkynes

Dialkyne compound is an important intermediate in organic synthesis,in recent years,scientists have paid more and more attention to the reaction which contains dialkynes,and some progress has been made in the cascade oxidation reaction of dialkynes catalyzed by Lewis acid.In this thesis,we mainly use NaBARF salt as a catalyst to catalyze the double oxidation reactions of dialkynes and the intermolecular oxidation and tandem cyclization reactions of dialkynes.The content is divided into the following two parts:In the first part,we have synthesized a series of pyrrolidone and piperidone derivatives through the double oxidation of dialkynes which is catalyzed by NaBARF.In traditional ways,these reactions are catalyzed by rhodium,gold and other noble metal catalysts.However,we only employ NaBARF to catalyze the double oxidation of 1,5-dialkynes,moreover,we extend the dialkyne compounds to 1,6-dialkynes,and get excellent results.Thus,this protocol provides a new and practical approach for the study of the double oxidation of dialkynes.In the second part,the intermolecular cascade oxidation reactions of 1,5-dialkynes catalyzed by NaBARF are studied to synthesize polycyclic aromatic compounds(PACs).On the basis of the work of the first part,the substrate is modified to make the intramolecular cyclization of dialkynes rather than the double oxidation reaction to synthesize tricyclic aromatic compounds.At the same time,we combine dialkynes with indole system to synthesize tetracyclic aromatic compounds with indole skeleton.The most important is that in this part,we introduce chiral centers in the substrate to produce new chiral centers in final product to realized asymmetric synthesis.It provides an important means for the asymmetric synthesis of dialkynes.