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

页码：2641 / 2652

页数：12

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