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Transition Metal‐Free Homocoupling of Unactivated Electron‐Deficient Azaarenes
Author(s) -
Xie WenWen,
Liu Yue,
Yuan Rui,
Zhao Dan,
Yu TianZhi,
Zhang Jian,
Da ChaoShan
Publication year - 2016
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500445
Subject(s) - chemistry , isoquinoline , transition metal , yield (engineering) , iridium , chloride , combinatorial chemistry , photochemistry , organic chemistry , catalysis , materials science , metallurgy
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.