Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (5): 1443-1452.DOI: 10.6023/cjoc202112018 Previous Articles     Next Articles



王馨瑶a,b, 张晴晴a, 刘书扬a, 李敏b,*(), 李海芳c,*(), 段春迎a,b, 金云鹤a,*()   

  1. a 大连理工大学张大煜学院 辽宁大连 116024
    b 大连理工大学化工学院 精细化工国家重点实验室 辽宁大连 116024
    c 清华大学化学系 生命有机磷化学及化学生物学教育部重点实验室 北京 100084
  • 收稿日期:2021-12-13 修回日期:2022-01-26 发布日期:2022-02-10
  • 通讯作者: 李敏, 李海芳, 金云鹤
  • 基金资助:
    国家自然科学基金(21901032); 国家自然科学基金(21775086); 中央高校基本科研业务费(DUT21LK13)

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

Xinyao Wanga,b, Qingqing Zhanga, Shuyang Liua, Min Lib(), Haifang Lic(), Chunying Duana,b, Yunhe Jina()   

  1. a Zhang Dayu School of Chemistry, Dalian University of Technology, Dalian, Liaoning 116024
    b State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian, Liaoning 116024
    c Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology, Ministry of Education, Department of Chemistry, Tsinghua University, Beijing, 100084
  • Received:2021-12-13 Revised:2022-01-26 Published:2022-02-10
  • Contact: Min Li, Haifang Li, Yunhe Jin
  • 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.

Key words: visible light-induced, metal-free synthesis, cross dehydrogenation coupling, C—H activation, quinones, benzylation