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Graphene Oxide Catalyzed C−H Bond Activation: The Importance of Oxygen Functional Groups for Biaryl Construction
Author(s) -
Gao Yongjun,
Tang Pei,
Zhou Hu,
Zhang Wei,
Yang Hanjun,
Yan Ning,
Hu Gang,
Mei Donghai,
Wang Jianguo,
Ma Ding
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.201510081
Subject(s) - catalysis , oxide , graphene , oxygen , chemistry , functional group , materials science , nanotechnology , organic chemistry , polymer
A heterogeneous, inexpensive, and environmentally friendly graphene oxide catalytic system for the C−H bond arylation of benzene enables the formation of biaryl compounds in the presence of aryl iodides. The oxygen functional groups in these graphene oxide sheets and the addition of KO t Bu are essential for the observed catalytic activity. Reactions with various model compounds and DFT calculations confirmed that these negatively charged oxygen atoms promote the overall transformation by stabilizing and activating K + ions, which in turns facilitates the activation of the C−I bond. However, the graphene π system also greatly facilitates the overall reaction as the aromatic coupling partners are easily adsorbed.