Litcius/Paper detail

Electrochemical C−H deuteration of pyridine derivatives with D2O

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

2024Nature Communications53 citationsDOIOpen Access PDF

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 D 2 O 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.

Topics & Concepts

PyridineElectrochemistryChemistryCyclic voltammetryCombinatorial chemistryIodideRegioselectivityMedicinal chemistryOrganic chemistryElectrodeCatalysisPhysical chemistryChemical Reactions and IsotopesAmmonia Synthesis and Nitrogen ReductionAsymmetric Hydrogenation and Catalysis