Recent Advance in Electrochemical Dehalogenative Deuteration

Authors

Peng-Fei Li, State Key Laboratory and Institute of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, Tianjin, 300071, China
Guang-Sheng Kou, State Key Laboratory and Institute of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, Tianjin, 300071, China
Li-Ping Qi, State Key Laboratory and Institute of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, Tianjin, 300071, ChinaFollow
You-Ai Qiu, State Key Laboratory and Institute of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, Tianjin, 300071, ChinaFollow

Corresponding Author

Li-Ping Qi(qiliping@nankai.edu.cn);
You-Ai Qiu (qiuyouai@nankai.edu.cn)

Abstract

In recent years, the incorporation of deuterium atoms into organic compounds has emerged as a vital focus in the development of pharmaceutical molecules. This trend is driven by the increasing recognition of the significance of compounds containing deuterium atoms across various domains, including materials and biopharmaceuticals, where they have found widespread applications in mechanistic studies within the realms of chemistry and biology. Meanwhile, organic electrochemistry, as a relatively environmentally friendly catalytic mode with broad adaptability to redox reactions, has emerged as a crucial alternative to traditional halogen-deuterium exchange in the context of the reduction deuteration of halides. This approach circumvents the uses of transition metal catalysts and toxic deuterated reagents which are commonly employed in traditional methods. Notably, electrocatalytic dehalogenation with deuterium incorporation typically relies on heavy water as the deuterium source, ensuring high yields and significant deuterium incorporation. In recent years, electrochemically dehalogenative deuteration of halides has made substantial progress, providing critical support for the synthesis and development of deuterated compounds. This article offers a comprehensive overview of the latest advancements in electrochemical reductive deuteration of both aromatic and alkyl halides, categorizing the progress according to the type of halide and delving into the underlying reaction mechanisms.

Graphical Abstract

Keywords

electrochemistry; deuteration; halide; deuterium oxide; dehalogenation

DOI Link

https://doi.org/10.61558/2993-074X.3442

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

Publication Date

2024-05-28

Online Available Date

2024-01-15

Revised Date

2024-01-03

Received Date

2023-10-29

Recommended Citation

Peng-Fei Li, Guang-Sheng Kou, Li-Ping Qi, You-Ai Qiu. Recent Advance in Electrochemical Dehalogenative Deuteration[J]. Journal of Electrochemistry, 2024 , 30(5): 2313005.
DOI: 10.61558/2993-074X.3442
Available at: https://jelectrochem.xmu.edu.cn/journal/vol30/iss5/1