Visible Light Catalytic Oxidation Reaction Of Amine Compounds

The natural abundant visible light has received widely attention for its characteristics of cheap,easily available,non-pollution and toxic-free.The application of visible light could not only solve the increasingly serious energy problem,but also is an effective method to satisfy the modern concept of green chemical synthesis.As the research going forward,the visible light catalysis was one of the most important ways to realize the C-H bond activation and the new C-C and C-X bond formation reactions.Recently,the visible light catalytic oxidation of amine compounds for the synthesis of nitrogen-containing compounds has made great progress,which was widely used in medicine,material and other fields.This dissertation consists of three chapters:The first chapter is a review of the oxidation of amine compounds catalyzed by visible light in recent years.And based on the difference of reaction mechanism,the application and significance of this method are introduced.In the second part,the reaction of aziridine and nitrile for the synthesis of imidazoline catalyzed by visible light has been developed.Under the visible light photoredox conditions,the highly selective ring opening of aziridines and subsequent coupling reaction with nucleophilic reagent is realized.Nitrile compounds showed good nucleophilic performance,a lot of imidazoline compounds with potential application were synthesized.Several kinds of aziridines and nitriles have good tolerance in this catalytic system.This reaction system shows high atom economy.While the nitrile was replaced by isothiocyanate,the ring addition product was also obtained.The application of this method successfully provides a new way to the synthesis of nitrogen-containing compounds.In the third part,the visible light photoredox coupling of amino acid derivatives with allenoate was studied.The method for the preparation of functionalized olefins via visible light catalysized-Michael addition reaction based on the free radical process is developed.On the one hand,amino acid derivatives as a class of functionalized tertiary amine in the visible light photocatalytic system could be oxidized and then lost one molecular of CO2 to give alkyl radical intermediate,which then reacted with allenoate;on the other hand,the experimental results showed that the allenoate in this free radical coupling reaction showed specific regioselectivity.