Work

2‐Fluoroanthraquinone‐Catalyzed Photooxidation of Benzylic Hydrocarbons and Aliphatic Alcohols With O 2 in Supercritical CO 2 , Accelerating Effect of Water

Year: 2026

Type: article

Abstract: A greener process for the oxidation of hydrocarbons containing primary, secondary, and tertiary benzylic carbon atoms, as well as aliphatic alcohols (e.g., cyclohexanol, menthol, and 4‐heptanol) with molecular oxygen in supercritical carbon dioxide (scCO 2 ) medium under the visible‐light irradiation in the presence of 2‐fluoroanthraquinone (2‐FAQ) as a photocatalyst (1 mol%) has been developed. The photooxidation reactions have been found to be accelerated by the addition of small amounts (1 equiv.) of water to the system. Plausible pathways for the promotion of the oxidation process have been identified: The most prominent is the cleavage of H─O bonds in the added water molecules under the action of the photocatalyst that results in extra reactive oxygen species generation. Also, a radical‐chain mechanism for the photocatalytic process has been proposed. It is the first time that experimental data on the photophysical properties of 2‐FAQ, including the redox potential of this promising photocatalyst in the photoexcited state, have been obtained.

Source: European Journal of Organic Chemistry

DOI: 10.1002/ejoc.70775

Authors: Vladislav G. Merkulov, Dmitry A. Kletnov, Vera I. Gladilina, Ilya V. Kuchurov, Mikhail N. Zharkov, Sergei G. Zlotin

Institutions: N.D. Zelinsky Institute of Organic Chemistry, National Research University Higher School of Economics, Moscow Institute of Physics and Technology

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: bronze

Funder: Russian Science Foundation

Award: G6886671717