University Chemistry ›› 2021, Vol. 36 ›› Issue (4): 2005019.doi: 10.3866/PKU.DXHX202005019

• Chemistry Laboratory • Previous Articles     Next Articles

Visible Light-Induced Synthesis of Ethyl 2, 2-Di(1H-indol-3-yl) acetate: Recommendation of a Green Organic Chemistry Experiment

Liqi Li, Xiaorong Yang, Yuan Zhang()   

  • Received:2020-05-07 Accepted:2020-06-22 Published:2020-07-06
  • Contact: Yuan Zhang E-mail:zhangyuan@lzu.edu.cn

Abstract:

Owing to its mild, clean, and environmentally benign characteristics, visible light-induced photoredox catalysis in the past few years has emerged as a powerful tool to trigger organic transformations; however, it has not been introduced into the undergraduate laboratory teaching. 3, 3'-Bisindolylmethanes (BIMs) are privileged structural units that exist widely in numerous pharmaceutical active molecules. Moreover, BIMs are also important synthetic intermediates of numerous alkaloid natural products. Recently, we developed a visible light-induced aerobic oxidative cross-coupling reaction of glycine derivatives with indoles, which provides a straightforward access to BIMs. On the basis of this work, we designed a semi-microscale organic chemistry experiment for the efficient synthesis of ethyl 2, 2-di (1H-indol-3-yl) acetate, starting from ethyl (4-methoxyphenyl) glycinate and indole by using Rhodamine 6G as the photocatalyst under the irradiation of visible light at room temperature. The aims are to promote students to broaden their horizon of knowledge, establish the concept of "green chemistry" and awareness of environmental protection through the introduction of innovative scientific research into the laboratory teaching.

Key words: Photoredox catalysis, Ethyl 2, 2-di(1H-indol-3-yl) acetate, Green chemistry, Undergraduate laboratory teaching

MSC2000: 

  • G64