Issue 4, 2022

Peroxide activation by selenium-doped graphite

Abstract

Selenium (Se), an essential trace element present in several antioxidant enzymes, is responsible for protecting cells from oxidative damage. In the recent past, a large number of naturally inspired Se-containing biomimetic molecular oxidation catalysts have been developed. In this report, a selenium-doped graphitic material (Se-DG) was synthesized using glucose and benzeneseleninic acid (BSA) via a simple hydrothermal method. Se-DG has shown glutathione peroxidase (GPx)-like activity and carried out epoxidation of various aromatic and aliphatic alkenes using H2O2, a green oxidant. In most cases, ∼90% conversion with ∼75% yield of epoxide was achieved in acetonitrile medium. The adduct of 5,5-dimethyl-1-pyrroline N-oxide (DMPO) with hydroperoxyl radical (˙OOH) was observed in HRMS which confirmed that the Se-DG produced ˙OOH from H2O2via hydrogen atom abstraction (HAA). A mechanistic insight of the olefin epoxidation was described in the presence of hydrocarbons and it was observed that the hydroxyl radical (˙OH) generated during the epoxidation facilitated C–H activation successfully. The plausible reaction mechanism of epoxidation was established with density functional theory (DFT) using Gaussian code.

Graphical abstract: Peroxide activation by selenium-doped graphite

Supplementary files

Article information

Article type
Paper
Submitted
09 Dec 2021
Accepted
06 Jan 2022
First published
07 Jan 2022

Catal. Sci. Technol., 2022,12, 1296-1312

Peroxide activation by selenium-doped graphite

S. Maity and B. B. Dhar, Catal. Sci. Technol., 2022, 12, 1296 DOI: 10.1039/D1CY02224E

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