碘化钾在芳香胺有机硒基化亲电取代反应中的催化应用

发布时间：2018-07-20 17:26

【摘要】：本论文主要研究了二硒醚化合物在催化量的碘化钾作用下芳香胺的有机硒基化亲电取代反应和在对甲苯磺酸作用下的烯烃硒基化亲电加成反应,全文共分为三个部分:1.文献综述部分。介绍了有机硒化合物的发展历程,有机硒化合物的合成方法,以及有机硒试剂作为亲电试剂,亲核试剂,催化剂在有机合成中的应用等。同时还介绍了有机硒化合物在生物药物方面的运用和有机硒药物的一些进展。2.碘化钾在芳香胺中有机硒基化亲电取代反应中的催化应用。针对现有合成有机硒基芳香胺方法中的一些不足,如使用重金属催化剂,反应试剂价格较高,原子利用率低等问题,采用了廉价的碘化钾作为催化剂和双氧水作为氧化剂,系统研究了二硒醚与芳香胺在室温条件下的有机硒基化亲电取代反应,经济,高效地得到了一系列具有区域选择性的硒醚。提出了该反应的可能反应机理。3.对甲苯磺酸作用下烯烃的硒化加成反应。我们研究了二硒醚在对甲苯磺酸和氧化剂间氯过氧苯甲酸作用下,室温条件下甲醇溶剂中与烯烃的亲电加成反应。优化了反应条件,提出了该反应的可能反应机理:二硒醚首先断裂成硒正离子,然后与烯烃形成硒摀中间体,最后在溶剂甲醇作用下产生硒基化加成产物。
[Abstract]:In this paper, the electrophilic substitution of aromatic amines by organic selenylation and the electrophilic addition of olefin by p-toluenesulfonic acid were studied under the catalysis of potassium iodide. The whole thesis is divided into three parts: 1. Literature review part. The development of organic selenium compounds, the synthetic methods of organic selenium compounds and the application of organic selenium reagents as electrophilic reagents, nucleophilic reagents and catalysts in organic synthesis were introduced. At the same time, the application of organic selenium compounds in biopharmaceuticals and the progress of organic selenium drugs are also introduced. Catalytic application of potassium iodide in electrophilic substitution of organic selenium in aromatic amines. In view of the shortcomings of the existing methods for the synthesis of organic selenyl aromatic amines, such as heavy metal catalysts, high price of reaction reagents and low atomic utilization rate, cheap potassium iodide was used as catalyst and hydrogen peroxide as oxidant. A series of selenoethers with regioselectivity were prepared by electrophilic substitution of organic selenylation with aromatic amines at room temperature. The possible reaction mechanism of the reaction was proposed. Selenium addition reaction of olefin under p-toluenesulfonic acid. The electrophilic addition reaction of diselenide with olefins in methanol solvent at room temperature under the action of p-toluenesulfonic acid and m-chloroperoxybenzoic acid was studied. The reaction conditions were optimized and the possible reaction mechanism of the reaction was put forward. The diselenide first breaks into selenium positive ion, then forms selenium as intermediate with olefin, and finally produces selenylation addition product under the action of solvent methanol.
【学位授予单位】：浙江工业大学
【学位级别】：硕士
【学位授予年份】：2016
【分类号】：O621.251

【相似文献】