Sn Mediated “One-Pot” Allylation Of Acylhydrazone In Water

Along with the development of green chemistry, more and more reactions were required to more friendly with environment and atomic economy in order to meet the requirments of green chemistry. The strategy of organic reaction using water as solvent and the avoiding of using toxic regants have draws attention of some chemists.Compared with traditional organic solvents, water as solvent in organic reactions have a lot of advantages: it can avoid the use of inflammable organic solvents; reactive functional groups, such as hydroxyl and carboxyl, don't need to protect and deprotect when water used as solvent.Organotins have been widely used because of their easy availability, air and moisture stability, tolerance to functional groups and high selectivity. However, most of stannanes are toxic. Furthermore, only one group in Organotins is delivered into the product molecules and the other residues are usually discarded as waste after the reactions.The thesis described an efficient process for synthesis of N?-homoallylic hydrazides. The paper provides a highly efficient and simple method to the synthesis of N?-homoallylic hydrazide compounds. The method has the important meaning for the synthesis of N?-homoallylic hydrazide compounds and the application of organotin reagents in organic synthesis.The thesis mainly consists of the following three parts:The first chapter: Progress of C-C Bonds Formations in Aqueous MediaThis chapter presents an overview of tremendous studies towards recent advances in progress of C-C bonds formations in aqueous media.The second chapter: Sn Mediated “One-Pot” Allylation of Acylhydrazone in WaterThis chapter explores the “one-pot” synthesis of homoallylic hydrazides from aldehydes or ketones, benzoylhydrazines, allylic bromide promoted by tin powder in water. In this process, water is used as solvent. Allylic bromide and tin powder is used to replace the toxic allylic stannane reagents. Therefor, it is an environmentally benign and efficient process for synthesis N'-homoallylic hydrazides. N-Acylhydrazines is found more reactive than amines in these processes. They can react not only with aldehydes but also with ketones to give corresponding N'-homoallylic hydrazides, but amines do not react with ketones to afford the products.The third chapter: Copper Catalyze Cross-couple Reaction of aryldiazoesterThis chapter explores the copper catalyze the cross-couple reaction of aryldiazoester with allybromine and copper catalyzed multicomponent reaction of aryl diazonium methyl acetate, methol and benzoyl hydrazone.