Issue 21, 2022
From the journal:

Chemical Communications

Potassium tert-butoxide promoted regioselective deuteration of pyridines†

Yan Li,ab   Chenxu Zheng,ab   Zhi-Jiang Jiang, ORCID logo *a   Jianbo Tang,ac   Bencan Tang ORCID logo d  and  Zhanghua Gao ORCID logo *a  

* Corresponding authors

a School of Biological and Chemical Engineering, NingboTech University, Ningbo, People's Republic of China
E-mail: zj.jiang@nbt.edu.cn, z.gao@nbt.edu.cn

b College of Chemical and Biological Engineering, Zhejiang University, Hangzhou, People's Republic of China

c College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, People's Republic of China

d Department of Chemical and Environment Engineering, The University of Nottingham Ningbo China, Ningbo, People's Republic of China

Abstract

A regioselective deuteration at the β- and γ-position of pyridines is reported. Efficient deuteration occurred with a combination of KOtBu 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.

Graphical abstract: Potassium tert-butoxide promoted regioselective deuteration of pyridines

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Article information

DOI
https://doi.org/10.1039/D1CC07128A
Article type
Communication
Submitted
20 Dec 2021
Accepted
11 Feb 2022
First published
14 Feb 2022

Chem. Commun., 2022,58, 3497-3500

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Potassium tert-butoxide promoted regioselective deuteration of pyridines

Y. Li, C. Zheng, Z. Jiang, J. Tang, B. Tang and Z. Gao, Chem. Commun., 2022, 58, 3497 DOI: 10.1039/D1CC07128A

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