自组装协同催化高选择性合成卤代芳烃

引用本文: 史时辉, 李皓瑜, 韩少杰, 姚一凡, 刘思齐. 自组装协同催化高选择性合成卤代芳烃[J]. 大学化学, 2024, 39(5): 336-344. doi: 10.3866/PKU.DXHX202312002 shu

Citation: Shihui Shi, Haoyu Li, Shaojie Han, Yifan Yao, Siqi Liu. Regioselectively Synthesis of Halogenated Arenes via Self-Assembly and Synergistic Catalysis Strategy[J]. University Chemistry, 2024, 39(5): 336-344. doi: 10.3866/PKU.DXHX202312002 shu

自组装协同催化高选择性合成卤代芳烃

延安大学化学与化工学院, 陕西延安 716000
基金项目:
延安大学教改项目(YDJG17-11)

摘要: 卤代芳烃是非常重要的合成砌块，广泛应用于农用化学品、材料和药物等的合成。芳烃的亲电取代卤化反应是制备芳基卤化物最简单的方法，但是富电子芳烃的卤化反应存在区域选择性差的挑战。本实验采用自组装协同催化策略，以环己基苯溴化反应为模型反应，高选择性合成溴代芳烃，进而应用于卤代芳烃的高选择性合成。在加深学生芳烃亲电取代卤化反应的同时，也向学生传授自组装、协同催化和路易斯酸碱催化等重要知识，加深学生对亲电取代反应机理和离子型中间体的了解。实验主要由卤代芳烃的合成、机理探究及实验普适性三部分组成，包含多种有机实验基本操作，涉及反应监测、分离纯化、产物表征等多个重要环节，实验整体时长7小时，安全性高，可操作性强，适合本科实验教学开设。本实验秉持科研反哺教学的理念，将新的科研成果转化为人才培养内容，有助于提高学生的科研创新与实践能力。

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English

Regioselectively Synthesis of Halogenated Arenes via Self-Assembly and Synergistic Catalysis Strategy

College of Chemistry and Chemical Engineering, Yan’an University, Yan’an 716000, Shaanxi Province, China
Received Date: 04 December 2023
Revised Date: 05 January 2024

Abstract: Electrophilic halogenation of arenes represents a fundamental method for synthesizing aryl halides, crucial in the construction of various agrochemicals, materials, and pharmaceuticals. However, achieving regioselectivity in the halogenation of electron-rich arenes has posed a persistent challenge. This experiment demonstrates a synergistic catalytic approach for halogenating arenes bearing electron-donating substituents under mild conditions, offering a highly selective pathway to aryl halides. The utilization of hydrogen bonding between a Brønsted acid and the protic solvent nitromethane facilitates this transformation, effectively addressing the aforementioned challenge. The experiment not only enhances students’ understanding of electrophilic halogenation reactions of arenes but also imparts knowledge on self-assembly, synergistic catalysis, and Lewis acid-base catalysis. Furthermore, it deepens students’ comprehension of reaction mechanisms and ionic intermediates. The experiment comprises three main components: synthesis of brominated aromatics, mechanism exploration, and applicability assessment. It encompasses various organic laboratory techniques, including reaction monitoring, purification, and product characterization. With a duration of 7 hours and ensuring high safety, this experiment is suitable for undergraduate teaching. Moreover, it serves to strengthen students’ fundamental experimental skills while fostering their capacity for scientific research innovation and practice, preparing them for future scientific endeavors.

Key words:

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自组装协同催化高选择性合成卤代芳烃

English

Regioselectively Synthesis of Halogenated Arenes via Self-Assembly and Synergistic Catalysis Strategy

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

自组装协同催化高选择性合成卤代芳烃

English

Regioselectively Synthesis of Halogenated Arenes via Self-Assembly and Synergistic Catalysis Strategy

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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