铜催化C-H活化在喹啉类衍生物合成中的应用

摘要本文探究了通过铜催化C-H键活化反应合成喹啉砜类衍生物的方法，筛选出了合成反应的最优条件，探究了该反应对各种底物的适应性，并对反应机理做了初步推测。该方法以易于制备和购得的喹啉酰胺以及磺酰氯为底物进行磺酰化反应，实验操作简便，反应条件温和，能够适应多种不同的底物，且使用的是廉价的铜系催化剂，所得到的目标化合物具有潜在的生物医药活性但以其它方法却难以合成，并且能够实现相当高的产率，符合绿色化学的原则。该方法为合成具有医药研究价值的喹啉砜类衍生物提供了新的途径，同时也拓展了铜系催化剂在有机合成和催化领域的应用。47659

Abstract: An effective synthetic route to quinoline derivatives via copper-catalyzed activation of C-H bonds was explored in this paper. Optimization Studies was conducted and the scope of the reaction was investigated. Probable mechanism for the sulfonation process was also proposed. With facile aminoquinolines and sulfonyl chloride as the substrates, various bioactive sulfonated quinolone products that would be difficult to synthesize by other methods were obtained in good yields. The reaction shows an excellent tolerance to a number of functional groups and the condition is simple and mild with inexpensive as the. This new C-S coupling reaction allows the preparation of valuable products a more effective synthetic route with high atom economy and promotes green chemistry. Meanwhile, it also expands applications of copper-based catalysts in synthetic and catalytic research fields.

毕业论文关键词：喹啉砜类；铜催化； C-H活化；磺酰化；绿色化学；

Keyword: quinoline derivatives; copper-based catalysts; activation of C-H bonds; sulfonation; green chemistry

1 引言 4

1.1 C-H键活化形成C-S键的研究背景 4

1.2 C-H键活化形成C-S键途径的最新研究进展 4

过渡金属催化C-H键活化 4

1.2.1 钯系催化剂 5

1.2.2 铜系催化剂 8

1.2.3 钌系催化剂 12

非金属催化C-H键活化 14

1.2.4 DTBP作为氧化剂 14

1.2.5 I2作为氧化剂 15

1.2.6 其他类型的催化体系 16

1.3 未来研究方向 16

1.4 选题意义 16

2 实验部分 17

2.1 实验仪器及试剂 17

2.2 铜催化C-H键活化合成喹啉砜类化合物反应的探究及条件的优化 19

2.2.1 反应的初步探究 19

2.2.2 催化剂的筛选 22

2.2.3 溶剂的筛选 22

2.2.4 反应助剂碱的筛选 23

2.2.5其他反应条件的筛选 24

2.3 反应的底物适应性研究 25

2.3.1 普适性探究实验的方案、步骤及技术路线 25

2.3.2 结果与讨论 26

3 结论 48

参考文献 48

致谢 50

1 引言铜催化C-H活化在喹啉类衍生物合成中的应用:http://www.youerw.com/huaxue/lunwen_49840.html