Experimental Study On Diazocompound Under Visible Light Photocatalytic

Since the first synthesis of ethyl diazoacetate by Curtius in 1883, diazocarbonyl compounds have attracted continuous attention for more than a century owing to their intrinsic high reactivity. Diazocompounds can be decomposed by three different reactive intermediates under the light, Lewis acid, metals conditions, which could be a active reaction intermediate for a series of reaction, such as Wolff rearrangement, cyclopropanation, C-H insertion, X-H insertion, oxygen ylide formation, nucleophilic addition et.al. Vinyldiazo reagents are versatile build three-carbon building blocks to access carbo- or heterocyclic frameworks. The first chapter of thesis an introduction about the above outlined.In the second chapter, we have described a visible-light induced aza-Darzens reaction of N-phenylglycine and diazocompounds. Various mono-substituted were obtained by using organic dye Rose Bengal as the photocatalyst, the reaction has wide substrate scope, and the yield could be up to 92%.N-Arylglycine derivatives represent important synthetic intermediates or building blocks for the drug development and natural-product synthesis. The N-arylglycine moiety also occurs in several bioactive natural products. The third chapter demonstrated the oxidative cyclization of N-arylglycine derivatives and diazocompounds. Depending on the conditions, aziridines and indoles were obtained as the products, but in the most cases, aziridines were the major products.Vinyldiazo compound is a three-carbon building blocks to access carbo- or heterocyclic frameworks through metal-catalyzed cycloadditions or other transformations. The fourth part demonstrated discovery thetrifluoromethylation of vinyldiazo compounds. The reaction uses of trifluoromethyl iodide as a source of trifluoromethyl radical, and the reaction occurs under visible light photoredox condition.