Transition Metal-Free Homocoupling of Unactivated Electron-Deficient Azaarenes

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• 作者：Wen-Wen Xie ; Yue Liu ; Rui Yuan ; Dan Zhao ; Tian-Zhi Yu ; Jian Zhang and Chao-Shan Da
• 关键词：azaarenes ; CC homocoupling ; tetramethylethylenediamine (TMEDA) ; 2 ; 2 ; 6 ; 6-tetramethylpiperidinylmagnesium chloride (TMPMgCl) ; transition metal-free conditions
• 刊名：Advanced Synthesis & Catalysis
• 出版年：2016
• 出版时间：March 17, 2016
• 年：2016
• 卷：358
• 期：6
• 页码：994-1002
• 全文大小：567K
• ISSN：1615-4169

文摘

This work has established the first direct homocoupling of unactivated electron-deficient azaarenes in the presence of TMPMgCl (2,2,6,6-tetramethylpiperidinylmagnesium chloride) and TMEDA (tetramethylethylenediamine). In this process, no transition metal was used while freely available air was employed as the oxidant. The investigated successful substrates included quinolines, isoquinoline, 3-phenylated pyridines, and 2-phenylated quinoxalines, giving moderate to high yields. The homocoupling of quinolines was effectively scaled up to one gram in high yield. Additionally, an iridium complex of 6,6′-dimethyl-2,2′-biquinoline was prepared and characterized as an efficient red-emitting material.