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Mixed Directing‐Group Strategy: Oxidative C−H/C−H Bond Arylation of Unactivated Arenes by Cobalt Catalysis
Author(s) -
Du Cong,
Li PengXiang,
Zhu Xinju,
Suo JianFeng,
Niu JunLong,
Song MaoPing
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201607719
Subject(s) - chemistry , transmetalation , metalation , aryl , benzamide , catalysis , pyridine , radical , deprotonation , cobalt , oxidative addition , reactivity (psychology) , combinatorial chemistry , oxidative phosphorylation , medicinal chemistry , organic chemistry , medicine , ion , biochemistry , alkyl , alternative medicine , pathology
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.