Palladium-catalyzed Allylation Of 1-phenyl-1-propyne

The transition metal catalyzed allylation reaction provides a convenient and efficient path for building carbon-carbon bonds,carbon-nitrogen bonds,carbon-oxygen bonds,and which has become an important means of organic synthesis.As an important way for the synthesis of allyl derivatives,it has been widely used in medicine,chemicals,pesticides and other fields.Therefore,the development of new effective allylation reaction has become a hot topic for chemical workers.In this dissertation,we have achieved the allylation of 1-phenyl-1-propyne with p-toluenesulfonylhydrazide and hydroxyquinazoline by palladium catalysis,respectively.Allyl sulfoxide compounds and allyl quinazoline compounds were synthesized in good yields with high regioselectivites.1.The allylation of 1-phenyl-1-propyne and p-toluenesulfonylhydrazide catalyzed by palladium catalyst was established for the first time.The reaction conditions were optimized and the substrate scope was examined.The reaction has good substrate adaptability and a series of allyl sulfoxide products were achieved in high yields.By control experiments,we proposed a plausible mechanism that involved π-allyl palladium intermediates.Sulfone compounds have biological activities such as weeding,disinsection,sterilization and antiviral,play an important role in the field of pesticides and pharmaceuticals.This experiment provides a new,simple and effective method for the synthesis of allylsulfone compounds.2.The allylation of 1-phenyl-1-propyne and hydroxyquinazoline catalyzed by palladium catalyst was achieved for the first time.,and the substrate was extended to a series of allyl quinazoline compounds.Heterocyclic compounds can be used as dyes,spices and drugs in chemical,biological and other fields widely.The synthesis of allyl quinazoline heterocyclic compounds,enriched the variety and synthetic methods of heterocyclic compounds.