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

引用本文: 邹子燕, 孙承博, 刘春燕, 李晓驰, 冯鹏举. 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[J]. 大学化学, 2023, 38(4): 336-346. doi: 10.3866/PKU.DXHX202212008 shu

Citation: Ziyan Zou, Chengbo Sun, Chunyan Liu, Xiaochi Li, Pengju Feng. Design of the Experiment for Time-Dependent Electrochemical Oxidative Coupling/Coupling-Cyclization of Indoles[J]. University Chemistry, 2023, 38(4): 336-346. doi: 10.3866/PKU.DXHX202212008 shu

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

暨南大学化学与材料学院, 广州 510632

通讯作者: 冯鹏举, pfeng@jnu.edu.cn

基金项目:
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。

关键词:

English

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

College of Chemistry and Materials Science, Jinan University, Guangzhou 510632, China

Corresponding author: Pengju Feng, pfeng@jnu.edu.cn

Received Date: 04 December 2022

Abstract: 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.

Key words:

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通讯作者: 陈斌, bchen63@163.com

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沈阳化工大学材料科学与工程学院沈阳 110142

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

通讯作者: 冯鹏举, pfeng@jnu.edu.cn

English

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

Corresponding author: Pengju Feng, pfeng@jnu.edu.cn

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

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

通讯作者: 冯鹏举, pfeng@jnu.edu.cn

English

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

Corresponding author: Pengju Feng, pfeng@jnu.edu.cn

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

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