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2-Bromoanthraquinone as a highly efficient photocatalyst for the oxidation of sec-aromatic alcohols: experimental and DFT study

Shengfu Liao,Jianguo Liu,Long Yan,Qiying Liu,Guanghui Chen,Longlong Ma

Anthraquinones are recognized as high efficiency photocatalysts which can perform various redox reactions in aqueous or organic phases. We have experimentally proven that 2-BrAQ can undergo hydrogen transfer with an alpha-aromatic alcohol under light conditions, thereby efficiently oxidizing the aromatic alcohol to the corresponding product. The yield of 1-phenethanol to acetophenone can reach more than 96%. In subsequent catalyst screening experiments, it was found that the electronegativity of the substituent at the 2 position of the anthraquinone ring and the acidity of the solvent affect the photocatalytic activity of anthraquinones. After using various aromatic alcohol substrates, 2-BrAQ showed good conversion and selectivity for most aromatic alcohols, but showed C–C bond cleavage and low selectivity with non-α-position aromatic alcohols. In order to explore the mechanism of the redox reaction of 2-BrAQ in acetonitrile solution, the corresponding free radical reaction pathway was proposed and verified by density functional theory (DFT). Focusing on calculations for 2-BrAQ during the reaction and the first-step hydrogen transfer reaction between the 2-BrAQ triplet molecule and the 1-phenylethanol molecule, we recognized the changes that occurred during the reaction and thus have a deeper understanding of the redox reaction of anthraquinone compounds in organic systems.