Palladium-catalyzed Denitrogenative Coupling Reaction

Transition metal catalyzed coupling reactions have become an extremely important method for preparing complex organic molecules such as drugs.Common transition metal catalyzed coupling reactions include the Heck reaction,Suzuki reaction,Negashi reaction,Hiyama reaction,Sonogashira reaction and the Heck reaction and the Suzuki reaction are particularly important.In addition to traditional carbon-halogen bond initiated coupling reactions,transition metal catalyzed coupling reactions initiated by the cleavage of inert chemical bonds such as carbon-oxygen,carbon-hydrogen,and carbon-carbon bonds have become a very important new field in organic chemical and organic metal chemistry,in which the cleavage of carbonnitrogen bonds,especially transition metal-catalyzed carbon-nitrogen bond cleavage,is less explored.The dissociation energy of the carbon-nitrogen bond is very high,so it is very stable,and when it is not activated,the reaction has the advantages of good selectivity,high yield,and few synthetic steps,and therefore it is increasingly being used in organic synthesis.The coupling reactions of aryl hydrazines and their derivatives have been greatly developed in recent years and are used to synthesize various types of biaryls,aryl olefins and other compounds.Recent studies have found that aryl hydrazine can not only undergo oxidative radical coupling reaction,but also undergo transition metalcatalyzed cross-coupling reaction.This type of reaction is diverse,the reaction system is flexible,and has potential for wide application in scientific and industrial research..In addition,the free radical coupling of nitrogen atoms of aryl hydrazine to selectively construct carbon-nitrogen bonds has important research value and application prospects for the synthesis of structurally diverse and potentially biologically active hydrazine derivatives.In this dissertation,N-acetyl modified arylhydrazine was selected as the starting material.Pd-catalyzed denitrification Heck coupling reaction with olefins and palladium-catalyzed denitrification Suzuki coupling reaction with phenylboronic acid compounds were used.In the Heck reaction,various functional group-substituted N-acetyl modified aryl hydrazine derivatives as well as various olefins can be reacted to obtain the target compound and have a moderate to good yield,providing a synthetic aryl olefin compound pathway;In the Suzuki reaction,various functional group-substituted aryl hydrazine derivatives and various functional groupsubstituted arylboronic acids react to synthesize biaryl compounds at room temperature.This reaction has the advantages of mild reaction conditions and good yield.