Gold-catalyzed Alkynes Cyclization For The Construct Tetrahydroquinoline And Naphthalene Derivatives

From this century,homogeneous gold catalysis has become a research focus,therefore this field has developed rapidly.Under homogeneous conditions,gold(?/?)complexes are the most effective catalysts for the electrophilic activation of alkynes.The most common reaction is the cyclization of alkynes.This type reaction can efficiently build C-C bond or C-X bond with the participation of gold catalysts.The advantages of gold catalyst system are mild reaction conditions and wide range of substrates.In this thesis,two types of cyclization reactions of gold-catalyzed alkyne bonds are mainly studied to efficiently construct tetrahydroquinoline compounds and naphthalene compounds.It mainly includes the following two parts:The first work mainly studies the cyclization/cycloaddition cascade reaction of gold-catalyzed alkynol and N-arylimine.The homogeneous gold catalyst played two roles in this reaction.One is to catalyze the intramolecular cyclization of alkynols;the other is to promote the[4+2]cyclization reaction.The reaction have the characteristics of high yield and high stereoselectivity,and provides a simple and efficient method for the synthesis of tetrahydroquinoline compounds.The second work mainly studies the gold-catalyzed intramolecular cyclization of alkyne-diazo compounds.In this reaction system,the gold catalyst preferentially activates the alkyne bond,then the diazo-compounds releases N2 after nucleophilic attack on the activated alkyne bond to form gold carbene.Finally the reaction terminates by aromatization to form disubstituted naphthalene ring compounds.This reaction has undergone 6-endo-dig cyclization,and a novel gold carbene intermediate has been constructed in situ.Further research is expected to find new carbene reactions.