Chinese Journal of Organic Chemistry >
Visible-Light-Driven Oxidation of Benzylic C—H Bonds Enabled by Anthraquinone in Water
Received date: 2024-08-13
Revised date: 2024-09-16
Online published: 2024-10-11
Supported by
Xi'an Medical University(2023BS30); Shaanxi Provincial Department of Education(24JK0646); National College Students’ Innovation and Entrepreneurship Training Program(202311840007)
An efficient photochemical protocol for the oxidation of alkylarenes to ketones was developed using anthraquinone (AQ) as a organic small molecule photocatalysts, O2 as an oxidant and water as green solvent. The main feature of this method is that visible light, molecular oxygen and water are low-cost, abundance and eco-friendliness in green chemistry. Moreover, the system shows a broad substrate scope and good functional-group tolerance, which can also easily be scaled-up to gram scale. A series of control experiments was conducted to study the influence of superoxide radicals on the reaction, and a reasonable catalytic cycle mechanism was proposed. The mechanism studies revealed that AQ absorbed the light and served as a photosensitizer to promote the transformation of O2 to the highly reactive $\text{O}_{2}^{\centerdot }$ via single electron transfer (SET) process, which then oxidized alkylarenes to ketones.
Key words： visible-light photocatalysis; alkylarene; ketone; anthraquinone; water
Chen Duan , Siyu Shen , Yuqi Zhao , Yue Liu , Xinyu Li , Lizhi Zhang , Wenjing Li . Visible-Light-Driven Oxidation of Benzylic C—H Bonds Enabled by Anthraquinone in Water[J]. Chinese Journal of Organic Chemistry, 2025 , 45(4) : 1352 -1359 . DOI: 10.6023/cjoc202406032
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