反应时间调控的电化学吲哚氧化偶联/偶联环化反应实验设计  

Design of the Experiment for Time-Dependent Electrochemical Oxidative Coupling/Coupling-Cyclization of Indoles

作　　者：邹子燕 孙承博 刘春燕 李晓驰 冯鹏举 Ziyan Zou;Chengbo Sun;Chunyan Liu;Xiaochi Li;Pengju Feng(College of Chemistry and Materials Science,Jinan University,Guangzhou 510632,China)

机构地区：[1]暨南大学化学与材料学院,广州510632

出　　处：《大学化学》2023年第4期336-346,共11页University Chemistry

基　　金：广东省基础与应用基础基金(2019A1515011743);广东省珠江人才计划青年拔尖人才(2017GC010302)。

摘　　要：吲哚类杂环化合物相关转化是有机化学基础知识。本实验以近年来快速发展的有机电合成技术为手段,以电子为清洁的反应试剂,实现了3-芳基吲哚的脱氢氧化偶联,进而仅延长反应时间即可获得偶联-环化的产物。实验涉及脱氢偶联、串联环化反应等,是重要的有机转化反应。本实验反应现象丰富,所用试剂安全,涉及操作丰富,有助于学生对实验架设、实验观察、实验处理、结果分析的全流程训练。实验经多人多次均可以相近产率重现,产物为固体,可由硅胶柱色谱纯化,结构可通过核磁共振波谱和质谱进行解析,产物具有丰富的荧光性质。该实验立足吲哚转化有机化学基础知识,利用电合成策略,开发含氮杂环化合物的实用合成方法,引导学生注重学习有机化学与物理化学交叉知识,建立学科交叉知识认知,关注学科发展前沿。The transformation reactions of indole derivatives are fundamental knowledge in organic chemistry.Using electrons as clean reagents,electrochemistry serves as a sustainable alternative to traditional redox organic transformations and received considerable attention in recent years.In this study,3-aryl indole was used as raw materials to realize dehydrogenation coupling and coupling-cyclization only by prolonging the electrolysis reaction time.The reaction runs under mild conditions and the reaction operation is simple and safe.The reaction is efficient to gain product in good yield and can be monitored by using thin-layer chromatography.There are various reaction phenomena for students to observe.Moreover,the final product of the reaction is controllable via simply tuning the reaction time.The experiment can be reproduced with similar efficiency after many times.All products are solid and can be purified via silica gel column chromatography.Nuclear magnetic resonance(NMR)spectroscopy and high resolution mass spectrometry(HRMS)were recorded to analyze the structure of products which also show different fluorescence properties.Based on the basic knowledge of indole transformation chemistry,this experiment uses green electrolysis strategies to develop practical synthesis methods for nitrogen-containing heterocyclic compounds,and guides students to learn interdisciplinary knowledge of organic synthesis chemistry and physical chemistry,establishes interdisciplinary knowledge awareness and pays attention to the frontiers of organic chemistry.

关 键 词：吲哚衍生物 C―C偶联反应 多步反应 电有机合成 产物可调反应 

分 类 号：G64[文化科学—高等教育学] O6[文化科学—教育学]