Copper-Catalyzed Bifunctionalization Reactions Of Organic Halides

Organic halides are important organic intermediates and the basic raw materials in the chemical industry.They have wide applications in the pharmaceutical,dye,agricultural,resource and environmental industries.Functionalized products developed by various halides have become an indispensable part of human society,enriching people’s lives.In chemical production involving halides,halide ions are commonly present as leaving groups,which are eventually discharged into the environment as "three wastes" and cause environmental pollution.In this context,the development of mild,efficient and highly selective halogen atom transfer reaction strategies are of great theoretical and application value from the viewpoint of raw material cost control and environmental protection,and is also very much in line with the connotation of green chemistry.This thesis investigates and compares the different halogen atom transfer reactions caused by nitrogen-containing coupling reagents with acyl halides oralkyl bromides respectively,and comprises the following two parts:In chapter two,we investigated the copper-catalyzed acylation halogenation of 3-methylanthranils with acyl halides.The reaction utilized acyl halides as the acyl and halogen sources to achieve an efficient synthesis of a series of N-(2-(2-haloyl)phenyl)amides compounds by cleaving the N-O/C-H/C-X bonds and forming C-N/C-X bonds.This difunctional conversion needs the N-O bond and oxygen as oxidants,and it is carried out under mild conditions.In the meantime,the substrate functional groups exhibit good tolerance.In chapter three,we investigated we investigated the copper-catalyzed N-alkylation and bromination of arylamines/indazoles with alkyl bromides.This chapter provides a detailed analysis of the N-alkylation-C-4 bromination reaction and the N,N-dialkylation-C-4bromination reaction between alkyl bromides and aryl amines,as well as the N-alkylation-C-3bromination reaction between alkyl bromides and imidazoles.Alkyl bromides in the reaction serve as both alkyl source and bromine source,with the good atom and procedure economy.This method is characterized by economical raw materials,mild conditions of reactions,easy operation,easy separation of products,wide applicability of substrates,and good compatibility with functional groups.Oxygen and water are respectively the oxidant and by-product of the reaction,which also meets the requirements of green chemistry.