钯催化C-H键活化氧化羰基化反应构建多元杂环化合物

发布时间：2018-05-29 07:05

本文选题：钯 + C-H键活化　；参考：《江西师范大学》2017年硕士论文

【摘要】：C-H键广泛存在于天然产物、化工产品、医药分子、功能材料中,它的高效官能团化一直是有机合成的核心问题。近年来,钯催化的C-H键活化反应逐渐发展成为C-H键选择性转化的重要手段,引起了广泛关注,并成为新的有机合成研究热点。而作为其中一种重要类型,钯催化C-H键活化/羰基化反应将重要的无机小分子——CO作为连接子引入到有机物产物中,成为绿色高效构建羰基类衍生物的重要工具。基于以上的背景,我的工作围绕这方面展开,主要分为以下两部分:1.我们通过钯催化氧化双C-H键活化/羰基化反应合成Fluorazones衍生物。这类衍生物具备重要生物活性,在医药生物领域具有重要的应用潜力。反应使用氯化钯作为催化剂,醋酸铜作为共催化剂,氧气作为氧化剂,实现了从N-芳基吡咯一步合成Fluorazones衍生物。该体系可以兼容富电子,贫电子,卤素等基团。而进一步机理实验证明第二步芳环C-H键活化可能是反应的决速步。2.我们成功实现了钯催化亚胺导向芳基C-H键活化/羰基化反应,一步实现由简单易得的亚胺到邻苯二甲酰亚胺类衍生物的合成。该反应条件相对简单,产率高,对底物的兼容性好。而邻苯二甲酰亚胺类衍生物在生物医药以及材料领域具有十分重要的应用。
[Abstract]:C-H bond widely exists in natural products, chemical products, pharmaceutical molecules, functional materials, its high efficiency functional group has been the core problem of organic synthesis. In recent years, palladium catalyzed C-H bond activation has gradually developed into an important means of selective conversion of C-H bond, which has attracted wide attention and become a new research hotspot in organic synthesis. As one of the important types, palladium catalyzed C-H bond activation / carbonylation reaction introduced important inorganic small molecules, CO as connectors, into organic products, and became an important tool for green and efficient construction of carbonyl derivatives. Based on the above background, I work around this area, mainly divided into the following two parts: 1. Fluorazones derivatives were synthesized by palladium catalyzed oxidation of double C-H bond activation / carbonylation reaction. These derivatives have important biological activity and have important application potential in the field of pharmaceutical biology. Fluorazones derivatives were synthesized from N-arylpyrrole by using palladium chloride as catalyst, copper acetate as co-catalyst and oxygen as oxidant. The system can be compatible with rich electron, poor electron, halogen and other groups. The further experimental results show that the activation of C-H bond in the second step may be the decisive step of the reaction. The palladium catalyzed aryl C-H bond activation / carbonylation reaction was successfully realized, and the synthesis of phthalimide derivatives from a simple and easily available imine was achieved in one step. The reaction condition is relatively simple, the yield is high, and the substrate compatibility is good. Phthalimide derivatives have important applications in biomedicine and materials.
【学位授予单位】：江西师范大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O626

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