Nature Communications (May 2024)

Electrochemical C−H deuteration of pyridine derivatives with D2O

  • Zhiwei Zhao,
  • Ranran Zhang,
  • Yaowen Liu,
  • Zile Zhu,
  • Qiuyan Wang,
  • Youai Qiu

DOI
https://doi.org/10.1038/s41467-024-48262-9
Journal volume & issue
Vol. 15, no. 1
pp. 1 – 9

Abstract

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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.