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Efficient Metal-Free Catalytic Reaction Pathway for Selective Oxidation of Substituted Phenols

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Su,  Dang Sheng
Shenyang National Laboratory for Materials Science Institute of Metal Research, Chinese Academy of Science;
Inorganic Chemistry, Fritz Haber Institute, Max Planck Society;

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Citation

Lin, Y., Li, B., Feng, Z., Kim, Y. A., Endo, M., & Su, D. S. (2015). Efficient Metal-Free Catalytic Reaction Pathway for Selective Oxidation of Substituted Phenols. ACS Catalysis, 5(10), 5921-5926. doi:10.1021/acscatal.5b01222.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0028-D580-E
Abstract
Selective oxidation of substituted phenols to p-benzoquinones is known to be inefficient because of the competing C–O coupling reaction caused by phenoxy radicals. The poor stability of conventional metal-based catalysts represents another bottleneck for industrial application. Here, we describe a metal-free reaction pathway in which onion-like carbon (OLC) as a low-cost catalyst exhibits excellent catalytic activity and stability in the selective oxidation of mono-, di- and trisubstituted phenols to their corresponding p-benzoquinones, even better than the reported metal-based catalysts (e.g., yield, stability) and industrial catalysts for particular substrates. Together with XPS, Raman, DFT calculations, and a series of comparative experiments, we demonstrate that the zigzag configuration as a type of carbon defects may play a crucial role in these reactions by stabilizing the intermediate phenoxy radicals.