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J Org Chem ; 87(6): 3978-3988, 2022 03 18.
Article in English | MEDLINE | ID: mdl-35254832

ABSTRACT

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 Csp3-H bonds to ketones and esters, giving excellent product yields (of up to 98% yield) without organic solvents at low O2 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.


Subject(s)
Nitrogen , Yeast, Dried , Carbon/chemistry , Catalysis , Nitrogen/chemistry , Oxygen , Phosphorus , Saccharomyces cerevisiae
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