title: Graphene Oxide Catalyzed C-H Bond Activation: The Importance of Oxygen Functional Groups for Biaryl Construction.
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.
authors.affiliation: Beijing National Laboratory for Molecular Sciences, College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871, China.
authors.forename: Yongjun
authors.initials: Y
authors.lastname: Gao
authors.affiliation: Beijing National Laboratory for Molecular Sciences, College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871, China.
authors.forename: Pei
authors.initials: P
authors.lastname: Tang
authors.affiliation: College of Chemical Engineering, Zhejiang University of Technology, Hangzhou, 310032, China.
authors.forename: Hu
authors.initials: H
authors.lastname: Zhou
authors.affiliation: Beijing National Laboratory for Molecular Sciences, College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871, China.
authors.forename: Wei
authors.initials: W
authors.lastname: Zhang
authors.affiliation: Beijing National Laboratory for Molecular Sciences, College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871, China.
authors.forename: Hanjun
authors.initials: H
authors.lastname: Yang
authors.affiliation: Department of Chemical and Biomolecular Engineering, National University of Singapore, 4 Engineering Drive 4, 117585, Singapore, Singapore.
authors.forename: Ning
authors.initials: N
authors.lastname: Yan
authors.affiliation: Israel Chemicals Limited, Shanghai, 200021, China.
authors.forename: Gang
authors.initials: G
authors.lastname: Hu
authors.affiliation: Institute for Integrated Catalysis, Pacific Northwest National Laboratory, Richland, WA, 99352, USA.
authors.forename: Donghai
authors.initials: D
authors.lastname: Mei
authors.affiliation: College of Chemical Engineering, Zhejiang University of Technology, Hangzhou, 310032, China. jgw@zjut.edu.cn.
authors.forename: Jianguo
authors.initials: J
authors.lastname: Wang
authors.affiliation: Beijing National Laboratory for Molecular Sciences, College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871, China. dma@pku.edu.cn.
authors.forename: Ding
authors.initials: D
authors.lastname: Ma
keywords: arylation; carbon; graphene oxide; heterogeneous catalysis