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Heterogeneous carbon nitride photocatalyst for C–C bond oxidative cleavage of vicinal diols in aerobic micellar medium

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Abstract

A green and efficient visible-light promoted aerobic oxidative C–C bond cleavage of vicinal diols in micellar medium has been developed. This protocol used graphitic carbon nitride with nitrogen vacancies (CN620) as a metal-free recyclable photocatalyst and CTAB as surfactant in water. Control experiments and the ESR results indicated that superoxide radicals and valence band holes played an important role in the reaction. Further isotope experiments suggested both a β-scission/HAT pathway and an oxidation/hydrolysis/dehydration pathway for the reaction, which is different from previous reports. The semiconductor/micellar catalyst system can be recycled at least 10 times without a significant reduction in activity. Furthermore, this reaction could be carried out under solar light irradiation and was applicable to large-scale reactions with similar results.

Graphical abstract: Heterogeneous carbon nitride photocatalyst for C–C bond oxidative cleavage of vicinal diols in aerobic micellar medium

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Supplementary files

Article information


Submitted
21 May 2020
Accepted
23 Jun 2020
First published
25 Jun 2020

Green Chem., 2020, Advance Article
Article type
Paper

Heterogeneous carbon nitride photocatalyst for C–C bond oxidative cleavage of vicinal diols in aerobic micellar medium

T. Niu, S. Chen, M. Hong, T. Zhang, J. Chen, X. Dong and B. Ni, Green Chem., 2020, Advance Article , DOI: 10.1039/D0GC01727B

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