创新性思维培养实验:基于“去芳香化-重新芳香化”策略实现水相条件下吲哚与酮的还原偶联反应  

Creative Thinking Cultivation Experiment:Reductive Cross-Coupling of Indoles with Ketones in Water via Dearomatization-Rearomatization Strategy

作　　者：郭佳聪 杨洋[1] 马明远 段戴平 曾会应 GUO Jia-Cong;YANG Yang;MA Ming-Yuan;DUAN Dai-Ping;ZENG Hui-Ying(The State Key Laboratory of Applied Organic Chemistry,College of Chemistry and Chemical Engineering,Lanzhou University,Lanzhou 730000,China;Institute of Higher Education,Lanzhou University,Lanzhou 730000,China)

机构地区：[1]兰州大学功能有机分子化学国家重点实验室化学化工学院,甘肃兰州730000 [2]兰州大学高等教育研究院,甘肃兰州730000

出　　处：《化学教育（中英文）》2024年第12期44-49,共6页Chinese Journal of Chemical Education

基　　金：教育部人文社会科学研究青年基金(19YJC880020);中国高等教育学会理科教育专业委员会高等理科教育研究课题(21ZSLKJYYB06);兰州大学教育教学改革研究项目;兰州大学课程思政示范课程建设项目。

摘　　要：传统实验教学是以培养学生“动手”能力为目的,主要以培养和夯实学生的“三基”(基本理论、基本知识、基本技能)为目标。然而对创新型人才的社会需求要求学校开设创新性实验,将以“三基”训练为目的转变为以“三基”和创新思维与能力训练为目标,培养学生既“动手”也“动脑”的能力和习惯。本实验打破了传统理论教学中吲哚与酮反应时一般发生在C-3位的观点,通过采用“去芳香化-重新芳香化”策略成功实现了反应位点选择性调控,完成了吲哚N位与酮的还原烷基化反应。本实验以吲哚和环戊酮为原料,甲酸为氢源,Pd(OH)2/C为催化剂,实现了在水相条件下吲哚N位和酮的还原缩合反应。本实验将书本中原有的知识点与新的反应策略结合,能够在实验教学的过程中提高学生对于知识的灵活运用能力和对科研的兴趣,培养学生的逆向思维和创新能力。Traditional experimental teaching aimed at cultivating students'"hands-on"ability and consolidating students'"three basics"(basic theory,basic knowledge and basic skills).However,in the face of the social demand for innovative talents,schools are required to set up innovative experiments for improving to creative thinking and ability training.The purpose is to cultivate students'abilities and habits of both"hands-on"and"minds-on".This new experiment breaks the traditional view that the reaction between indole and ketone usually occurs at the C-3 position in the theoretical teaching,and successfully realizes the selective change of reaction site via"dearomatization-rearomatization"strategy,achieving reductive N-alkylation of indole.In this experiment,indole and cyclopentanone were used as starting materials,formic acid as the hydrogen source,and Pd(OH)2/C as the catalyst to synthesis of N-alkylation indole under aqueous phase conditions.This experiment combines the original knowledge in books with innovative reaction strategies,which can improve students'ability to apply their knowledge flexibly and their interests in research during the experimental teaching process,and cultivate students'reverse thinking and innovative ability.

关 键 词：创新思维 逆向思维 去芳香化-重新芳香化策略 探究式教学 

分 类 号：O621.251-4[理学—有机化学] G642.423[理学—化学]