Chinese Journal of Organic Chemistry >
Visible Light-Induced Metal-Free Benzylation of Quinones via Cross Dehydrogenation Coupling Reaction
Received date: 2021-12-13
Revised date: 2022-01-26
Online published: 2022-02-10
Supported by
National Natural Science Foundation of China(21901032); National Natural Science Foundation of China(21775086); Fundamental Research Funds for the Central Universities(DUT21LK13)
Benzylated quinones widely exist in natural products and drug molecules. Thus their convenient synthesis with high efficiency brings great significance. However, hard conditions are still essential among the present reports. Herein, the development of visible light-induced metal-free benzylation of quinones via cross dehydrogenation coupling reaction with methylene blue as photocatalyst, tert-butyl hydroperoxide as oxidant, and toluene derivatives as benzylation reagent is reported. The reaction exhibits many advantages, including mild conditions, a broad scope with good functional group tolerance, low cost, and avoidance of metal remaining in products. This method may bring novel inspiration and approach for synthesis of bioactive quinones.
Xinyao Wang , Qingqing Zhang , Shuyang Liu , Min Li , Haifang Li , Chunying Duan , Yunhe Jin . Visible Light-Induced Metal-Free Benzylation of Quinones via Cross Dehydrogenation Coupling Reaction[J]. Chinese Journal of Organic Chemistry, 2022 , 42(5) : 1443 -1452 . DOI: 10.6023/cjoc202112018
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