碱催化C-S偶联反应——“绿色的”巯基-马来酰亚胺点击化学教学实验

Alkali-Catalyzed C-S Coupling Reaction: A “Green” Teaching Experiment of Thiol-maleimide Click Chemistry

介绍了一个简单实用"绿色的"巯基-马来酰亚胺点击化学教学实验:在二氯甲烷中混合等摩尔N-对氟苯基马来酰亚胺和2,5-二氯苯硫酚及微量三乙胺催化剂,经由经典的巯基,不饱和酮1,4加成反应,即可在短时间内完成C-S偶联反应;实验后处理简单有效,高纯度产物由反应后溶液中直接结晶析出,其结构经由核磁共振氢谱鉴定.此教学实验具备"点击化学"和"绿色化学"的核心特点,耗时短、操作简便、反应进程可视化、拥有100%原子经济性,是一个优秀的本科化学教学实验.

A ＂green＂ and convenient teaching experiment of thiol-maleimide click chemistry is introduced： simply mixing the 1-（4-fluorophenyl）-lH-pyrrole-2,5-dione and 2,5-dichlorobertzenethiol with the catalyst of triethylamine in dichloromethane yields high pure C-S coupling product in a short time. Its mechanism is the classic 1,4-addition of enone with thiol-nucleophile. After the reaction, the recrystallization from the reaction solvent of dichloromethane affords the pure product which is pure enough to be determined by 1H NMR. The teaching experiment has the critical characters of ＂Click Chemistry＂ and ＂Green Chemistry＂ with 100% atom efficiency. The visual process of reaction from yellowish to lilac increases the interest of students. This teaching experiment of thiol-maleimide click chemistry is an excellent experiment for undergraduate students.