Pd-Catalyzed N-Arylations of 3-Aryl-1-tosyl-1H-pyrazol-5-amines with Arylbromides and the Migration of Ts Group

被引：6
|
作者：
He, Jing [1 ]
Yang, Zhen [1 ]
Li, Weiwei [1 ]
Wei, Yueting [1 ]
Dai, Bin [1 ]
Zhao, Jixing [1 ]
Liu, Ping [1 ]
机构：
[1] Shihezi Univ, Sch Chem & Chem Engn, Key Lab Green Proc Chem Engn Xinjiang Bingtuan, Shihezi City 832004, Peoples R China
来源：
CHEMCATCHEM | 2021年 / 13卷 / 11期
基金：
中国国家自然科学基金;
关键词：
Pd-catalysis; C− N coupling; 1H-pyrazol-5-amine; migration; arylation; Ts group; aryl bromides;
D O I：
10.1002/cctc.202100193
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
An efficient palladium-catalyzed N-arylations of 3-aryl-1-tosyl-1H-pyrazol-5-amines with arylbromides is established. A series of diversified N-arylated products are obtained in excellent yields with broad substrate scope. Importantly, the N-arylated products undergo 1,4- and 1,6-migration reactions of Ts group under the action of Cs2CO3, affording the N-Ts-substituted pyrroles as major products (1,6-migration). Similar results can also be directly obtained by palladium-catalyzed reactions of 3-aryl-1-tosyl-1H-pyrazol-5-amines with arylbromides in the presence of Cs2CO3 as a base. Mechanistic studies reveal that the Ts-migration is achieved through an intermolecular pathway.
引用
收藏
页码：2641 / 2652
页数：12
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