Transamidation via C-N bond cleavage of amides and tertiary amines

被引：23
|
作者：
Idris, Muhammad Aliyu [1 ]
Lee, Sunwoo [1 ]
机构：
[1] Chonnam Natl Univ, Dept Chem, Gwangju 61184, South Korea
来源：
ORGANIC CHEMISTRY FRONTIERS | 2020年 / 7卷 / 18期
基金：
新加坡国家研究基金会;
关键词：
CATALYZED TRANSAMIDATION; PRIMARY CARBOXAMIDES; SECONDARY AMIDES; CARBOXYLIC-ACIDS; DIRECT AMIDATION; HECK REACTION; ACTIVATION; AMINOCARBONYLATION; UREAS;
D O I：
10.1039/d0qo00713g
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The C-N bond of tertiary amines was activated in the presence of a palladium catalyst and peroxide and subsequently reacted with tertiary amides to provide transamidated products in good yields. The protocol exhibited a broad substrate scope. The optimal conditions were determined as: PdCl2(2 mol%), KI (10 mol%), NH4Cl (10 mol%) and di-tert-butylperoxide (DTBP), in anisole at 100 degrees C.N-Benzoylglutarimide,N-phenyl-N-tosylbenzamide,N-Boc-N-phenylbenzamide and benzoyl saccharin were successfully coupled with tertiary amines. The palladium catalyst and DTBP are likely involved in the cleavage of the C-N bond of tertiary amines to provide the corresponding secondary amines.
引用
收藏
页码：2737 / 2743
页数：7
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