Cu-catalyzed Electrochemical C-H Fuctionalization

In last several years,the rapid expansion of the global economy and the rapid consumption of global resources has led to environmental pollution and the destruction of human ecological environment.Therefore,developing green economy,green technology and create a green life is highly demanded.Similarly,it is important to find the green and economical synthesis methods in organic chemical synthesis.So organic electrochemical synthesis has become one of the popular research fields in organic chemistry.Because it uses green,safe and environmental friendly electrons as redox reagents,which avoids the use of the toxic,expensive and stoichiometric oxidants.In addition,the rate and chemical selectivity of reactions could be turning by changing the amount of current and voltage.Meanwhile,the merger of electrochemical oxidation and transition metal has emerged as a powerful tool in organic chemistry.Therefore,it is appearing to find cheap and highly reactive metals to be used as electrocatalysts to promote the reaction.Copper,which located in the first subgroup of fourth cycle of the periodic table,is a cheap,readily available,abundant and low-toxic metal.Therefore,we developed copper-catalyzed electrochemical C-H fuctionalization of8-aminoquinoline and cyclic tertiary amine.The first part:We summarize the recent progress in the study of transition metal catalyzed electrochemical C-H fuctionalization.The second part:Copper-catalyzed electrochemical selective bromination of8-aminoquinoline amide using NH₄Br as the brominating reagent:we used the electrochemical oxidation instead of the traditional stoichiometric oxidant strategy,at the same time we use ammonium bromide not only as a source of bromine but also as the electrolyte,wich achieved the selective bromination of 8-aminoquinoline derivatives by controlling the current.The system does not require additional additives and oxidants,and the reaction mechanism is studied by cyclic voltammetry.The third part:Ligand-promoted copper catalyzed electrochemical decarboxylative coupling of cyclic tertiary amine with propargyl acids.In summary,the selective bromination of 8-aminoquinoline derivatives and the decarboxylation coupling of cyclic tertiary amine and propargyl acids were realized in this thesis by using copper as the electrocatalyst providing an environmentally tool for C-H fuctionalization.