Creative Thinking Cultivation Experiment: Reductive Cross-Coupling of Indoles with Ketones in Water via Dearomatization-Rearomatization Strategy
GUO Jia-Cong1, YANG Yang1, MA Ming-Yuan1, DUAN Dai-Ping2**, ZENG Hui-Ying1**
1. The State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000,China; 2. Institute of Higher Education, Lanzhou University, Lanzhou 730000,China
Abstract 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.
GUO Jia-Cong, YANG Yang, MA Ming-Yuan, DUAN Dai-Ping, ZENG Hui-Ying. Creative Thinking Cultivation Experiment: Reductive Cross-Coupling of Indoles with Ketones in Water via Dearomatization-Rearomatization Strategy[J]. Chinese Journal of Chemical Education, 2024, 45(12): 44-49.
