Mixed Directing-Group Strategy: Oxidative C-H/C-H Bond Arylation of Unactivated Arenes by Cobalt Catalysis

被引:97
作者
Du, Cong [1 ]
Li, Peng-Xiang [1 ]
Zhu, Xinju [1 ]
Suo, Jian-Feng [1 ]
Niu, Jun-Long [1 ]
Song, Mao-Ping [1 ]
机构
[1] Zhengzhou Univ, Coll Chem & Mol Engn, Kexue Ave 100, Zhengzhou 450052, Peoples R China
基金
中国国家自然科学基金;
关键词
arylation; biaryls; cross-coupling; cobalt; reaction mechanisms; CARBON-CARBON BONDS; MECHANISTIC INSIGHTS; SELECTIVE ACCESS; CARBOXYLIC-ACIDS; TERMINAL ALKYNES; ACTIVATION; ANNULATION; AMIDES; FUNCTIONALIZATION; ISOQUINOLINES;
D O I
10.1002/anie.201607719
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A mixed directing-group strategy for inexpensive [Co(acac)(3)]-catalyzed oxidative C-H/C-H bond arylation of unactivated arenes has been disclosed. This strategy enables the arylation of a wide range of benzamide and arylpyridines effectively to afford novel bifunctionalized biaryls, which are difficult to achieve by common synthetic routes. Two different pathways, namely, a single-electron-transmetalation process (8-aminoquinoline-directed) and a concerted metalation-deprotonation process (pyridine-directed), were involved to activate two different inert aromatic C-H bonds. Moreover, the aryl radicals have been trapped by 2,6-di-tert-butyl-4-methylphenol to form benzylated products. This unique strategy should be useful in the design of other arene C-H/C-H cross-couplings as well.
引用
收藏
页码:13571 / 13575
页数:5
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