Study On The Synthesis Of Benzazepine Based On Palladium-catalyzed Direct Functionalization Of C(sp~2)-H Bond

N-containing heterocyclic skeleton is the core structure of many natural products,pharmaceuticals and bioactive molecules.In addition,with the rapid development of catalytic chemistry,N-containing heterocyclic skeleton is increasingly appearing in organic catalysts and auxiliary ligands of transition-metal catalysts.The seven-membered nitrogen heterocycle is an indispensable member of the nitrogen-containing heterocycles.Therefore,the construction of seven-membered nitrogen heterocycle compounds has attracted considerable attention in synthetic chemistry community.In this paper,the synthetic methods of benzazepines were briefly introduced.In the light of these achievements,a more friendly strategy,based on C-H bond activation,to build benzo[b]azepine compounds was developed.The innovation of this strategy is the realization of direct oxidative coupling of anilines and alkenes employing allenes as a two-carbon linker,which also is the first time to be used in construction of benzoazepine compounds.This article consists of two parts.In recent years,the research on the synthesis of benzoazepine derivatives has made great progress,which provides effective access to naturally occurring and biologically active benzoazepines.In first part,the synthesis of azepine compounds were briefly introduced.In second part,we have developed an efficient method for the synthesis of benzo[b]azepine compounds based on Pd-catalyzed annulation of 2-vinylanilines involving allenes.It is the first implementation of the oxidative coupling of anilines and alkenes employing allenes as a two-carbon linker,which is attractive in terms of assembly efficiency and environmentally friendliness.The transformation features mild reaction conditions and good functional group tolerance,resulting in a variety of benzo[b]azepines in good to excellent yields.In addition,we also did preliminary investigation on the reaction mechanism.