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Catalytic Construction Of C-S Bonds By Copper And Electrochemical Oxidation Of NaX(Cl/Br) To Construct C-X Bond Reaction

Posted on:2020-01-19Degree:MasterType:Thesis
Country:ChinaCandidate:A J YaoFull Text:PDF
GTID:2381330575956109Subject:Organic Chemistry
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In the organic synthesis reaction,since the sulfur-containing group plays an important auxiliary role in the synthesis sequence,the application range of the organic sulfur chemistry is greatly increased.The formation of carbon-sulfur atom bonds is a key step in the synthesis of organic sulfur compounds.Organic sulfur compounds are inevitably present in many synthetic drugs and biologically active natural products.The formation of carbon-sulfur bonds is also a very important reaction in the process of forming an organism.Therefore,the carbon-sulfur bond-forming reaction has attracted the interest of many organic synthetic chemists who are actively exploring new ways to develop these reactions.Organic halides(R-X)are structural motifs ubiquitous in drug molecules and are key building blocks in the synthesis of fine chemicals.For the synthesis of organic halides,these methods typically require stoichiometric additives or oxidizing agents,metal catalysts,leaving groups or targeting groups,toxic halogenating agents,and the like.The complexity of the catalytic system also limits the applicability of these methods.Here,we report the halogenation of a clean electrochemically oxidized NaX.This paper is divided into the following two parts: one is based on aryl hydrazine and stilbene as raw materials,copper catalyzed reaction to synthesize ?-ketosulfone compounds;the other is NaX as halogenating reagent,electrochemical oxidation The next step is the efficient synthesis of organic halides.The main contents are as follows:1.A method for synthesizing ?-ketone sulfone compounds by using aryl hydrazine and stilbene as raw materials under the catalysis of copper bromide and oxygen as oxidant was developed.2.A method for chlorination and bromination of aromatic hydrocarbons by a clean electrochemical method using NaX as a halogenating reagent under electrochemical oxidation.The method has a wide range of applications and has reached the standard of gram-level synthesis.At the same time,the method has the advantages of simple operation,low toxicity or non-toxic halogenation reagent,green environmental protection,etc.,so that the halogenation reaction develops toward a clean and environmentally friendly direction.
Keywords/Search Tags:Carbon-sulfur bond, Copper catalyst, Organic halides, Electrochemical oxidation, halogenated
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