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- Title
Transition Metal-Free Homocoupling of Unactivated Electron-Deficient Azaarenes.
- Authors
Xie, Wen ‐ Wen; Liu, Yue; Yuan, Rui; Zhao, Dan; Yu, Tian ‐ Zhi; Zhang, Jian; Da, Chao ‐ Shan
- Abstract
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.
- Subjects
AZAARENES; COUPLING reactions (Chemistry); ELECTRON-deficient compounds; TRANSITION metal compounds synthesis; QUINOLINE; ISOQUINOLINE; PYRIDINE; QUINOXALINES
- Publication
Advanced Synthesis & Catalysis, 2016, Vol 358, Issue 6, p994
- ISSN
1615-4150
- Publication type
Other
- DOI
10.1002/adsc.201500445