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2022 , Vol. 42 >Issue 5: 1443 - 1452

DOI: https://doi.org/10.6023/cjoc202112018

研究论文

可见光诱导无金属条件下交叉脱氢偶联反应合成醌类苄基化衍生物

  • 王馨瑶 ,
  • 张晴晴 ,
  • 刘书扬 ,
  • 李敏 ,
  • 李海芳 ,
  • 段春迎 ,
  • 金云鹤
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  • 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

  网络出版日期: 2022-02-10

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)

收起

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

  • Xinyao Wang ,
  • Qingqing Zhang ,
  • Shuyang Liu ,
  • Min Li ,
  • Haifang Li ,
  • Chunying Duan ,
  • Yunhe Jin
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  • 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
*Corresponding authors. E-mail: ;
;
;

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)

Fold

摘要

苄基化醌类化合物广泛存在于天然产物及药物活性分子中, 对其进行简单高效的合成具有重要价值, 目前已有的醌类苄基化反应条件都较为苛刻. 介绍了一种以有机染料亚甲基蓝作为光敏剂, 叔丁基过氧化氢作为氧化剂, 在可见光照射条件下通过醌与甲苯衍生物之间的交叉脱氢偶联反应实现醌类化合物直接苄基化的新方法. 该方法具有条件温和、底物范围广泛、官能团兼容性好、成本低廉及能有效避免金属残留等诸多优势. 该方法的建立为醌类活性分子的合成及衍生化提供了新的思路和途径.

关键词： 可见光诱导; 无金属合成; 交叉脱氢偶联; 碳氢活化; 醌; 苄基化

本文引用格式

王馨瑶 , 张晴晴 , 刘书扬 , 李敏 , 李海芳 , 段春迎 , 金云鹤 . 可见光诱导无金属条件下交叉脱氢偶联反应合成醌类苄基化衍生物[J]. 有机化学, 2022 , 42(5) : 1443 -1452 . DOI: 10.6023/cjoc202112018

Abstract

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

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