Potassium tert-butoxide promoted regioselective deuteration of pyridines

Yan Li; Chenxu Zheng; Zhi-Jiang Jiang; Jianbo Tang; Bencan Tang; Zhanghua Gao

doi:10.1039/d1cc07128a

Potassium tert-butoxide promoted regioselective deuteration of pyridines

Chem Commun (Camb). 2022 Mar 10;58(21):3497-3500. doi: 10.1039/d1cc07128a.

Authors

Yan Li^{1

2}, Chenxu Zheng^{1

2}, Zhi-Jiang Jiang¹, Jianbo Tang^{1

3}, Bencan Tang⁴, Zhanghua Gao¹

Affiliations

¹ School of Biological and Chemical Engineering, NingboTech University, Ningbo, 315100, People's Republic of China. zj.jiang@nbt.edu.cn.
² College of Chemical and Biological Engineering, Zhejiang University, Hangzhou, 310012, People's Republic of China.
³ College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, People's Republic of China.
⁴ Department of Chemical and Environment Engineering, The University of Nottingham Ningbo China, Ningbo, 315100, People's Republic of China.

PMID: 35191912
DOI: 10.1039/d1cc07128a

Abstract

A regioselective deuteration at the β- and γ-position of pyridines is reported. Efficient deuteration occurred with a combination of KO^tBu and DMSO-d₆, replenishing the prevailing α-deuteration of the pyridine systems. Preliminary mechanistic studies suggested that the dimsyl carbanion acts as one of the key intermediates.