Electrochemical C−H deuteration of pyridine derivatives with D2O

Zhiwei Zhao, Ranran Zhang, Yaowen Liu, Zile Zhu, Qiuyan Wang () and Youai Qiu ()
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Zhiwei Zhao: Nankai University
Ranran Zhang: Nankai University
Yaowen Liu: Nankai University
Zile Zhu: Nankai University
Qiuyan Wang: Nankai University
Youai Qiu: Nankai University

Nature Communications, 2024, vol. 15, issue 1, 1-9

Abstract: Abstract Herein, we develop a straightforward, metal-free, and acid-/base-free electrochemical C4-selective C − H deuteration of pyridine derivatives with economic and convenient D2O at room temperature. This strategy features an efficient and environmentally friendly approach with high chemo- and regioselectivity, affording a wide range of D-compounds, such as pyridines, quinolones, N-ligands and biorelevant compounds. Notably, the mechanistic experiments and cyclic voltammetry (CV) studies demonstrate that N-butyl-2-phenylpyridinium iodide is a crucial intermediate during the electrochemical transformation, which provides a general and efficient way for deuteration of pyridine derivatives.

Date: 2024
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DOI: 10.1038/s41467-024-48262-9

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