Pyridinamide-directed Nickel-catalyzed Hydroarylation Of Alkenes And Remote Arylalkylation

Dicarbofunctionalization of alkenes provides access to complex organic molecules from simple raw materials,and has become an important research field in organic synthesis in recent years.A series of functionalization reactions for activated alkenes through various strategies have been reported.However,the development of new functionalization reactions of unactivated alkenes still faces great challenges.Inspired by the previous research in this field,we explored the hydro functionalization and dicarbofunctionalization of unactivated alkenes.This thesis mainly consists of two parts:In the first part,we investigated the nickel-catalyzed picolinamide-directed hydroarylation of unactivated alkenes.Using a directing group strategy,the hydroarylation reaction of unactivated alkenes with a series of arylboronic acids was achieved,and various linear hydroarylation products were synthesized.The reaction substrate has a wide range of substrate scope and excellent functional group compatibility.The generality of this method could be applied to late-stage modification of complex drug molecules.In the second part,we investigated nickel-catalyzed picolinamide-directed remote arylalkylation of unactivated alkenes.Based on previous work,we broadened the substrate to 5-hexenylamine substrates,explored difunctionalization reactions at remote sites,and investigated the diastereoselectivity of ?,?-substituted terminal and internal olefins.The reaction was found to be well suited for primary and secondary alkyl halides,as well as various arylboronic acid reagents,with excellent substrate compatibility.The picolinamide directing group participated in the formation of six-membered and seven-membered nickelcycle intermediates in this reaction,and achieved excellent regioselectivity and diastereoselectivity.Therefore,this method provides a new route for the precise synthesis of complex compounds.