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Studies Of Palladium-Catalyzed C-H Arylation And Copper-Catalyzed Cyanation Of Aryl Halides Reactions In PEG-400

Posted on:2017-08-02Degree:MasterType:Thesis
Country:ChinaCandidate:X Y ShangFull Text:PDF
GTID:2311330485477311Subject:Organic Chemistry
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With the development of chemistry, a considerable threat is presented in front of us. The traditional chemical industry has brought serious environment pollution,hundreds of millions of tons of hazardous waste are produced all around the world in every year, which causes serious harm to the environment, and threatens the survival of humanity. Therefore, the opinion of green chemistry was formed. Green chemistry refers to the "full utilization of resources, energy, non-toxic and harmless materials;the reaction is performed in a non-toxic, harmless condition, it reduces waste discharges to the environment and improves the utilization of atoms, all atomic materials have been transformed to products with zero emissions. This view is increasingly being advocated by chemists.Low molecular weight polyethylene glycol(PEG-400) as a new type of organic solvent, which is non-toxic, non-irritating, good thermal stability, non-flammable,inexpensive, recyclable and easy to recycle. It can dissolve a great of organic compounds with good compatibility, which is suitable for the development of green organic chemistry. It has been widely used in many reactions, including reduction,oxidation, hydrogenation reaction, asymmetric hydroxylation reaction, Heck reaction,Suzuki-Miyaura reaction, Michael addition and so on.This thesis contains two parts:In the first part, we studied the palladium-catalyzed ortho-arylation of benzoic acids using an aminoacetic acid as double chelated groups in PEG-400 as a medium.Excellent results were achieved and up to 95% yield of the C-H ortho-arylation product were obtained in this reaction system.In the secend part, we studied the copper-catalyzed cross-coupling reaction of aryl halides with Na2[Fe(CN)5NO].2H2 O in PEG-400. Compared with traditional cyanide reagent such as K4[Fe(CN)6], we found that the protocol presents better reactivity. Furthermore, when aryl bromides were used as coupling partners, high yields were obtained.
Keywords/Search Tags:PEG-400, C-H activation, aryl nitrile
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