Litcius/Paper detail

Selective Aerobic Oxidation of C<sub>sp<sup>3</sup></sub>–H Bonds Catalyzed by Yeast-Derived Nitrogen, Phosphorus, and Oxygen Codoped Carbon Materials

Zhaoyang Ju, Lina Song, Mingben Chong, Dang‐guo Cheng, Yang Hou, Ximing Zhang, Qinghua Zhang, Lanhui Ren

2022The Journal of Organic Chemistry21 citationsDOI

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.

Topics & Concepts

ChemistryCatalysisCarbon fibersHeteroatomYeastNitrogenPyrolysisOxygenYield (engineering)Inorganic chemistryPhosphorusOrganic chemistryRing (chemistry)MetallurgyComposite numberBiochemistryMaterials scienceComposite materialOxidative Organic Chemistry ReactionsCatalytic C–H Functionalization MethodsRadical Photochemical Reactions