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

Yan Li, Chenxu Zheng, Zhi Jiang Jiang, Jianbo Tang, Bencan Tang, Zhanghua Gao

Department of Chemical and Environmental Engineering

Research output: Journal Publication › Article › peer-review

18 Citations (Scopus)

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.

Original language	English
Pages (from-to)	3497-3500
Number of pages	4
Journal	Chemical Communications
Volume	58
Issue number	21
DOIs	https://doi.org/10.1039/d1cc07128a
Publication status	Published - 14 Feb 2022

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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10.1039/d1cc07128a

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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.",

author = "Yan Li and Chenxu Zheng and Jiang, {Zhi Jiang} and Jianbo Tang and Bencan Tang and Zhanghua Gao",

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AU - Li, Yan

AU - Zheng, Chenxu

AU - Jiang, Zhi Jiang

AU - Tang, Jianbo

AU - Tang, Bencan

AU - Gao, Zhanghua

PY - 2022/2/14

Y1 - 2022/2/14

N2 - 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.

AB - 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.

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U2 - 10.1039/d1cc07128a

DO - 10.1039/d1cc07128a

M3 - Article

C2 - 35191912

AN - SCOPUS:85126152401

SN - 1359-7345

VL - 58

SP - 3497

EP - 3500

JO - Chemical Communications

JF - Chemical Communications

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ER -

Potassium tert-butoxide promoted regioselective deuteration of pyridines

Abstract

ASJC Scopus subject areas

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