Sequential Sonogashira/intramolecular aminopalladation/cross-coupling of ortho-ethynyl-anilines catalyzed by a single palladium source: rapid access to 2,3-diarylindoles.
Sequential Sonogashira/intramolecular aminopalladation/cross-coupling of ortho-ethynyl-anilines catalyzed by a single palladium source: rapid access to 2,3-diarylindoles.
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DOI：
10.1039/d0ob02295k
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发表时间：
2021-01
影响因子：
3.2
通讯作者：
Jiwei Wang;Gendi Wang;Xiang Cheng;Ye Liu;Jun Zhang
中科院分区：
文献类型：
--
作者：
Jiwei Wang;Gendi Wang;Xiang Cheng;Ye Liu;Jun Zhang
我们开发了一种实用有效的一锅法合成2，3-二芳基吲哚的方法，通过钯催化的邻乙炔基苯胺与芳基碘的双芳基化环化反应。机理研究表明，Pd催化的Sonogashira反应首先发生，得到一个内部的炔中间体，随后经过分子内氨基钯化/交叉偶联得到2，3-二芳基吲哚。本发明的方法表现出广泛的底物范围，产生带有两个不同芳基的各种2，3-二芳基吲哚。
We have developed a practical and efficient one-pot protocol for the synthesis of 2,3-diarylindoles via Pd-catalyzed bis-arylative cyclization of various o-ethynylanilines with aryl iodides. Mechanism studies showed that a Pd-catalyzed Sonogashira reaction took place firstly, giving an internal alkyne intermediate, which subsequently underwent intramolecular aminopalladation/cross-coupling to give access to 2,3-diarylindoles. The present methodology exhibits a broad substrate scope, producing various 2,3-diaryl indoles bearing two different aryl groups.