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

Angewandte Chemie
Yongjun GaoDing Ma

Abstract

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

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Jun 2, 2017·Chemical Society Reviews·Sergio NavalonHermenegildo García
Dec 23, 2016·Chemical Communications : Chem Comm·Zhenzhen YangZhimin Liu
Jul 25, 2017·Organic & Biomolecular Chemistry·Changduo PanJin-Tao Yu
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Jun 10, 2020·Angewandte Chemie·Marco Bandini, Lorenzo Lombardi
Jul 9, 2021·Organic & Biomolecular Chemistry·Li YangFang Ke
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Oct 5, 2019·Organic Letters·Muhammad Sohail AhmadYuta Nishina
Jun 5, 2018·Organic Letters·Laura FavarettoMarco Bandini

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