Visible Light-Induced Metal-Free Benzylation of Quinones via Cross Dehydrogenation Coupling Reaction

被引：4

作者：

Wang Xinyao ^{[1
,2
]}

Zhang Qingqing ^{[1
]}

Liu Shu-yang ^{[1
]}

Li Min ^{[2
]}

Li Haifang ^{[3
]}

Duan Chun-ying ^{[1
,2
]}

Jin Yunhe ^{[1
]}

机构：

[1] Dalian Univ Technol, Zhang Dayu Sch Chem, Dalian 116024, Liaoning, Peoples R China

[2] Dalian Univ Technol, Sch Chem Engn, State Key Lab Fine Chem, Dalian 116024, Liaoning, Peoples R China

[3] Tsinghua Univ, Dept Chem, Key Lab Bioorgan Phosphorus Chem & Chem Biol, Minist Educ, Beijing 100084, Peoples R China

来源：

CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 42卷 / 05期

基金：

中国国家自然科学基金;

关键词：

visible light-induced; metal-free synthesis; cross dehydrogenation coupling; C-H activation; quinones; benzylation; ELECTRON-TRANSFER; C(SP(3))-H; ACIDS; PHOTOSENSITIZER; ALKYLATION; QUINOXALIN-2(1H)-ONES; FUNCTIONALIZATIONS; PEROXYDISULFATE; COUMARINS; THEILERIA;

D O I：

10.6023/cjoc202112018

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：1443 / 1452

页数：10

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