摘要本课题拟采用过渡金属催化碳氢键活化的导向基团定位的硝化反应，通过导向基团选择导向硝化，以期实现吲哚C2位绿色高效的选择性硝基化。过渡金属催化碳氢键活化的硝化反应，原子经济性强、环境友好；直接碳氢活化反应较传统硝化方式选择性更高，能较好的实现选择性硝化。本课题中进行的实验可以实现吲哚C2位硝化，但提高专一选择性、实现有效的产物分离有待进一步探索研究。实验结果表明该反应能更好地实现铜介导的基于碳氢键活化的吲哚类化合物的选择性偶联反应。实现C2位选择性的关键是装载在吲哚氮原子上可移除的嘧啶基导向基团，一系列的吲哚底物能够有效地在C2位置进行交叉脱氢耦合。该反应提供的2,2'-二吲哚是材料和制药工业中的至关重要的化合物。28959
关键词 碳氢键活化 吲哚 导向基团 硝化 偶联
毕业论文设计说明书外文摘要
Title C2-Nitration of Indoles via C-H Activation Assisted by a Removable Group
Abstract
This paper intends to pursue a nitration reaction via C-H activation catalyzed by transition metal,orientated by directing group,in order to achieve the C2-Nitration of indoles in a efficient and green way. This way is in conformity with the principle of atom economy, environmentally and friendly. Also，a higher selectivity can be achieved with the direct C-H activation method. The experiments in this paper can achieve the C2-nitration of indoles, but improve the selectivity and to achieve effective product separation remains to be further studied. Experimental results show that the reaction can better realize the Copper-Mediated direct C2-Homocoupling of indoles via C-H activation assisted by a removable pyrimidyl group.The installation of a removable pyrimidyl group on the indole nitrogen atom is the key for the C2 selectivity. A series of indole substrates underwent cross-dehydrogenative-homocoupling effectively at the C2 position, affording the corresponding 2,2'-biindole cores of fundamental importance in material and pharmaceutical chemistry.
Keywords C-H Activation / Indole / Directing group / Nitration / Homocoupling
目 次
1 引言 1
1.1 硝化反应的背景及意义 1
1.1.1 芳香族硝基化合物 2
1.1.2 吲哚及其衍生物 2
1.2 碳氢键活化的发展 3
1.2.1 碳氢活化的背景 3
1.2.2 碳氢活化的意义 3
1.2.3 碳氢活化的应用前景 4
1.2.4 导向基团的发展 4
1.3 过渡金属催化碳氢键硝化的反应进展 5
1.4 课题研究进展及应用背景 9
2 实验部分11
2.1 合成底物11
2.1.1 合成方法及原理11
2.1.2 实验试剂与仪器11
2.1.3 实验步骤12
2.2 吲哚硝化反应研究13
2.2.1 实验分析13
2.2.2 实验总结14
2.3 吲哚偶联反应研究14
2.4 条件优化15
2.5 底物扩展16
2.6 产物表征（NMR谱图见附录）17
3 结果与讨论 21
结论 22
致谢 23
参考文献24
附录 27 基于碳氢活化的吲哚硝化反应研究:http://www.751com.cn/huaxue/lunwen_24016.html