单一钯源催化的乙炔基苯胺的连续Sonogashira反应/分子内氨基钯化反应/交叉偶联反应：快速合成2,3-二芳基吲哚

Sequential Sonogashira/intramolecular aminopalladation/cross-coupling of -ethynyl-anilines catalyzed by a single palladium source: rapid access to 2,3-diarylindoles.

作者信息

Wang Jiwei, Wang Gendi, Cheng Xiang, Liu Ye, Zhang Jun

机构信息

Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry & Molecular Engineering, East China Normal University, 3663 North Zhongshan Road, Shanghai 200062, China.

Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, School of Chemistry and Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China.

出版信息

Org Biomol Chem. 2021 Feb 18;19(6):1329-1333. doi: 10.1039/d0ob02295k.

DOI:10.1039/d0ob02295k

PMID:33464262

Abstract

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.

摘要

我们已经开发出一种实用且高效的一锅法协议，用于通过钯催化各种邻乙炔基苯胺与芳基碘的双芳基化环化反应合成2,3-二芳基吲哚。机理研究表明，首先发生钯催化的Sonogashira反应，生成内部炔烃中间体，该中间体随后进行分子内氨基钯化/交叉偶联反应，从而得到2,3-二芳基吲哚。本方法具有广泛的底物范围，可生成带有两个不同芳基的各种2,3-二芳基吲哚。