Visible Light Induced Nitration Of Styrenes And Deacylation Arylation Of N-Acyl Benzotriazoles Catalysed By Copper Power

Visible light-induced photocatalytic reaction has been a powerful method for organic synthesis,which shows some advantages of environmental benign,high atom economy and good chemical selectivity.In recent years,visible light-induced photocatalytic reactions have been received extensive attention in organic synthesis.Diaryl iodide salts are highly electron-deficient high valent iodonium(?)salts which show good stability in air and in humidity.In recent years,diaryliodonium salts as electronphilic arylating agents have been widely used in organic synthesis.This thesis includes the following three chapters:Chapter 1:Research Progress in Application of Visible Light Induced Photocatalytic Reactions and Diaryliodonium Salts in Organic SynthesisA brief review has been described in this chapter.Firstly,visible light photosensitizers were introduced and the research progress in applications of VL-induced photocatalytic reactions in organic synthsis was reviewed briefly.Secondly,the structures,propenties and synthetic methods of diaryliodoniums were introduced.The application of diaryliodoniums as arylating agents in organic synthesis was also reviewed.Chapter 2:Visible light Induced Nitration of StyrenesIn this chapter,the nitration of styrenes under visible light irradition was studied in detail.A simple and efficient synthetic method for the preparation of nitrostyrenes was developed by using copper nitrate as a nitro source.Different VL sources and power were screened and reaction conditions were optimized.23 products were obtained in good to excellent yield with exclusively regioselectivity.The reaction mechanism was studied preliminany.This method shows wide substrate scope,good functional group tolerance and simple operation.Chapter 3:Copper Catalysed Deacylation Arylation of N-Acylbenzotriazoles with Diaryliodonium saltsAn efficient copper-catalyzed tandem deacylation arylation reaction of1-acyl-1H-1,2,3-benzotriazoles with diaryliodonium salts was explored.The reaction was conducted regioselectively to form 1-aryl-1H-1,2,3-benzotriazoles in MeCN at 80~oC in the presence of cesium carbonate.29 examples were given with the product yield of up to 84%.The probable reaction mechanism ws proposed based on our experiment observations and reported literatures.