铜促进的C-H键官能团化反应及三氟甲基菲啶的合成研究

发布时间：2019-03-31 15:45

【摘要】：过渡金属催化偶联反应是有机合成中构建碳杂键的重要手段之一。β卤代烯基硫醚,芳胺及含三氟甲基菲啶化合物都是重要的有机结构单元,广泛的存在于天然产物中。含这些结构单元的化合物具有重要的生物活性,并且经常运用于医药,农药,材料等领域。木文围绕β-卤代烯基硫醚,芳胺及含三氟甲基菲啶化合物的合成工作进行研究。本论文分为四部分:(1)论述了β-卤代烯基硫醚,芳胺及三氟甲基菲啶化合物的合成研究背景。(2)研究了铜促进的烯烃双官能团化反应。该三组分反应通过烯烃偶联合成βΝ卤代烯基硫醚,操作简单,原料廉价易得,实用性强。(3)研究了铜催化的C-H氨化反应,用于合成芳基胺类化合物,该反应底物适用性广。(4)研究了异腈参与的银催化环化反应,用于合成三氟甲基菲啶。该反应以廉价易得的三氟甲基亚磺酸钠为三氟甲基试剂,硝酸银作为催化剂。反应条件温和,产率中等至优秀。
[Abstract]:Transition metal catalytic coupling reaction is one of the important methods to construct carbon heterocyclic bonds in organic synthesis. 尾-haloenyl thioether, arylamine and trifluoromethyl phenanthroidine compounds are important organic structural units, which exist widely in natural products. Compounds containing these structural units have important biological activities, and are often used in medicine, pesticides, materials and other fields. The synthesis of 尾-haloenyl sulfides, arylamines and trifluoromethyl phenanthroidine compounds was studied in this paper. This thesis is divided into four parts: (1) the background of the synthesis of 尾-haloenyl thioether, arylamine and trifluoromethyl phenanthroidine is reviewed. (2) the copper-promoted bifunctional reaction of olefins is studied. This three-component reaction is simple in operation, cheap and easy to obtain, and practical. (3) the copper-catalyzed ammoniation of C, H, and arylamines is studied, which can be used to synthesize arylamines, and can be used in the synthesis of arylamines by using copper-catalyzed ammoniation reaction, which can be used to synthesize aromatic amines. This reaction substrate has a wide applicability. (4) the silver-catalyzed cyclization reaction involving isonitrile has been studied for the synthesis of trifluoromethyl phenanthroidine. In this reaction, sodium trifluoromethyl sulfite was used as trifluoromethyl reagent and silver nitrate was used as catalyst. The reaction conditions are mild and the yield is medium to excellent.
【学位授予单位】：温州大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O621.251;O626

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