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
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
收藏
页码:4300 / 4307
页数:8
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