Palladium-catalyzed tandem addition/cyclization in aqueous medium: synthesis of 2-arylindoles

被引：17

作者：

Yu, Shuling ^{[1
]}

Hu, Kun ^{[1
]}

Gong, Julin ^{[1
]}

Qi, Linjun ^{[1
]}

Zhu, Jianghe ^{[1
]}

Zhang, Yetong ^{[1
]}

Cheng, Tianxing ^{[1
]}

Chen, Jiuxi ^{[1
]}

机构：

[1] Wenzhou Univ, Coll Chem & Mat Engn, Wenzhou 325035, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2017年 / 15卷 / 20期

基金：

中国国家自然科学基金;

关键词：

ONE-POT SYNTHESIS; C-H ACTIVATION; DIRECT C-2 ARYLATION; ARYLBORONIC ACIDS; ARYL KETONES; ROOM-TEMPERATURE; REGIOSELECTIVE SYNTHESIS; REDUCTIVE CYCLIZATION; 2-SUBSTITUTED INDOLES; ORGANIC-REACTIONS;

D O I：

10.1039/c7ob00572e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient protocol to construct 2-arylindoles was developed through palladium-catalyzed tandem addition/cyclization of potassium aryltrifluoroborates with aliphatic nitriles in aqueous medium. The use of water as the reaction medium makes the synthesis process environmentally benign. A plausible mechanism for the formation of 2-arylindoles involving sequential nucleophilic addition followed by an intramolecular cyclization is proposed. Moreover, the utility of this catalytic tandem transformation was also demonstrated in an efficient gram-scale synthesis. This method provides an alternative synthetic tool for accessing a more diverse array of 2-arylindoles.

引用

页码：4300 / 4307

页数：8

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