Potassium tert-butoxide promoted regioselective deuteration of pyridines

被引:16
|
作者
Li, Yan [1 ,2 ]
Zheng, Chenxu [1 ,2 ]
Jiang, Zhi-Jiang [1 ]
Tang, Jianbo [1 ,3 ]
Tang, Bencan [4 ]
Gao, Zhanghua [1 ]
机构
[1] NingboTech Univ, Sch Biol & Chem Engn, Ningbo 315100, Peoples R China
[2] Zhejiang Univ, Coll Chem & Biol Engn, Hangzhou 310012, Peoples R China
[3] Lanzhou Univ, Coll Chem & Chem Engn, Lanzhou 730000, Peoples R China
[4] Univ Nottingham Ningbo China, Dept Chem & Environm Engn, Ningbo 315100, Peoples R China
关键词
HYDROGEN-DEUTERIUM EXCHANGE; NITROGEN-HETEROCYCLES; ISOTOPE-EXCHANGE; RHODIUM; ENHANCEMENT; TRITIUM;
D O I
10.1039/d1cc07128a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A regioselective deuteration at the beta- and gamma-position of pyridines is reported. Efficient deuteration occurred with a combination of (KOBu)-Bu-t and DMSO-d(6), replenishing the prevailing alpha-deuteration of the pyridine systems. Preliminary mechanistic studies suggested that the dimsyl carbanion acts as one of the key intermediates.
引用
收藏
页码:3497 / 3500
页数:4
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