Graphene Oxide Catalyzed C-H Bond Activation: The Importance of Oxygen Functional Groups for Biaryl Construction

被引：160

作者：

Gao, Yongjun ^{[1
]}

Tang, Pei ^{[1
]}

Zhou, Hu ^{[2
]}

Zhang, Wei ^{[1
]}

Yang, Hanjun ^{[1
]}

Yan, Ning ^{[3
]}

Hu, Gang ^{[4
]}

Mei, Donghai ^{[5
]}

Wang, Jianguo ^{[2
]}

Ma, Ding ^{[1
]}

机构：

[1] Peking Univ, Coll Chem & Mol Engn, Beijing Natl Lab Mol Sci, Beijing 100871, Peoples R China

[2] Zhejiang Univ Technol, Coll Chem Engn, Hangzhou 310032, Zhejiang, Peoples R China

[3] Natl Univ Singapore, Dept Chem & Biomol Engn, 4 Engn Dr 4, Singapore 117585, Singapore

[4] Israel Chem Ltd, Shanghai 200021, Peoples R China

[5] Pacific NW Natl Lab, Inst Integrated Catalysis, Richland, WA 99352 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 09期

关键词：

arylation; carbon; graphene oxide; heterogeneous catalysis; DIRECT ARYLATION; UNACTIVATED ARENES; CARBON MATERIALS; SP(2) CARBON; ARYL HALIDES; BENZENE; DEHYDROGENATION; OXIDATION;

D O I：

10.1002/anie.201510081

中图分类号：

O6 [化学];

学科分类号：

070301 [无机化学];

摘要：

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 KOtBu 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 system also greatly facilitates the overall reaction as the aromatic coupling partners are easily adsorbed.

引用

页码：3124 / 3128

页数：5

共 37 条

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Well-Defined Ruthenium(II) Carboxylate as Catalyst for Direct C-H/C-O Bond Arylations with Phenols in Water [J].