Selective Aerobic Oxidation of C sp 3 -H Bonds Catalyzed by Yeast-Derived Nitrogen, Phosphorus, and Oxygen Codoped Carbon Materials

Nitrogen, phosphorus, and oxygen codoped carbon catalysts were successfully synthesized using dried yeast powder as a pyrolysis precursor. The yeast-derived heteroatom-doped carbon (yeast@C) catalysts exhibited outstanding performance in the oxidation of C -H bonds to ketones and esters, giving exce...

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Veröffentlicht in:Journal of organic chemistry 2022-03, Vol.87 (6), p.3978-3988
Hauptverfasser: Ju, Zhao-Yang, Song, Li-Na, Chong, Ming-Ben, Cheng, Dang-Guo, Hou, Yang, Zhang, Xi-Ming, Zhang, Qing-Hua, Ren, Lan-Hui
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Sprache:eng
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Zusammenfassung:Nitrogen, phosphorus, and oxygen codoped carbon catalysts were successfully synthesized using dried yeast powder as a pyrolysis precursor. The yeast-derived heteroatom-doped carbon (yeast@C) catalysts exhibited outstanding performance in the oxidation of C -H bonds to ketones and esters, giving excellent product yields (of up to 98% yield) without organic solvents at low O pressure (0.1 MPa). The catalytic oxidation protocol exhibited a broad range of substrates (38 examples) with good functional group tolerance, excellent regioselectivity, and synthetic utility. The yeast-derived heteroatom-doped carbon catalysts showed good reusability and stability after recycling six times without any significant loss of activity. Experimental results and DFT calculations proved the important role of N-oxide (N -O ) on the surface of yeast@C and a reasonable carbon radical mechanism.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c02641