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Study on Copper Catalyzed C-S Cross-coupling of Using KF/Al2O3 as Base

Author: LiYuanYuan
Tutor: FengYiSi；XuHuaJian
School: Hefei University of Technology
Course: Biochemical Engineering
Keywords: Solid base KF/Al2O3 Ullmann reaction C-S coupling Halogenated aromatic hydrocarbons Thiophenol ( alcohol )
CLC: O643.32
Type: Master's thesis
Year: 2010
Downloads: 91
Quote: 0
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Abstract


CS is the synthesis of some key biochemical building , medicine, materials and other molecules critical step . The traditional method of building CS bond generally more demanding , high temperature if necessary , equivalents of copper reagent , longer reaction times and the yield is not high . Recent development of the transition metal-catalyzed coupling reaction , which overcomes the above disadvantages , that is containing a transition metal palladium, nickel , copper, iron , cobalt and indium compounds such as a catalyst , in a suitable amount of the ligand with or without the presence of the ligand can be achieved under relatively mild conditions with aryl halides thiophenol ( alcohol ) coupling reaction between . Given the needs of industrialization and environmental protection , research efficiency, low toxicity , inexpensive and environmentally friendly catalytic system has an important significance. Relative to palladium , it is a cheap and low toxicity of copper metal , copper catalyst used to achieve cross-coupling is not only a transition metal catalyzed a new trend in the field , and the chemical industry in the process of a green challenge subject. Based on extensive literature research as well as the basis of previous studies by our group , through a lot of influence on the reaction conditions, such as copper salts , solvents , temperature, concentration , reaction time and other studies , we found that a simple , innovative , efficient and economical copper CS bond catalyzed Ullmann -type coupling reaction : CuI (10 mol%), KF/Al2O3 (2.5 equiv), under N2 atmosphere , reaction temperature 110 ℃ reaction time 8 h at this approximation can be obtained under the conditions of the reaction equivalent yield . With the same type of reaction has been reported compared to the catalytic efficiency greatly improved , and the reaction can be completed only 8 h ; catalyst cheap and easy to get , without adding any ligand ; reaction operation is relatively simple ; reaction conditions relatively mild ; while the catalyst system a wide range of applications , the study found for a variety of substituted aromatic iodides , thiophenol aromatic , aliphatic and heterocyclic thiol compounds catalyzed coupling can be a good , high yield , and some catalytic reaction is almost quantitative . Therefore, we believe that the application of solid base KF/Al2O3 organic reactions will provide a new synthetic route .

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CLC: > Mathematical sciences and chemical > Chemistry > Physical Chemistry ( theoretical chemistry ),chemical physics > Chemical kinetics,catalysis > Catalytic > Catalytic reaction
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