有机化学 ›› 2016, Vol. 36 ›› Issue (2): 239-247.DOI: 10.6023/cjoc201512006 上一篇    下一篇

研究专题

可见光促进的自由基型三重键插入反应在多取代芳(杂)环合成中的应用 2017-2018 Awarded

孙晓阳, 俞寿云   

  1. 南京大学化学化工学院 生命分析化学国家重点实验室 南京 210023
  • 收稿日期:2015-11-03 修回日期:2015-12-15 发布日期:2015-12-21
  • 通讯作者: 俞寿云 E-mail:yushouyun@nju.edu.cn
  • 基金资助:

    国家自然科学基金(No. 21472084)资助项目.

Synthesis of Polysubstituted (Hetero)aromatic Compounds Using Visible-Light-Promoted Radical Triple Bond Insertions

Sun Xiaoyang, Yu Shouyun   

  1. State Key Laboratory of Analytical Chemistry for Life Science, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023
  • Received:2015-11-03 Revised:2015-12-15 Published:2015-12-21
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21472084).

综述了本课题组近年来在利用可见光促进的自由基型三重键插入反应合成多取代芳香化合物方面的研究进展.使用异腈插入反应构建了邻位取代吡啶、1-位取代异喹啉和6-位取代的菲啶衍生物; 使用炔烃插入反应合成了多取代的萘酚和呋喃及异喹啉酮衍生物; 还利用异腈/炔烃的多米诺插入反应构建了喹啉衍生物和异腈/氰基的多米诺插入反应构建了喹喔啉衍生物. 这些反应都是在可见光促进的光氧化还原条件下进行, 反应条件温和, 产率较高.

关键词: 光化学, 自由基, 炔烃, 异腈, 氰基, 芳香化合物

Synthesis of polysubstituted (hetero)aromatic compounds enabled by visible-light-promoted radical triple bond insertions has been reviewed. A series of polysubstituted naphthols, furans and isoquinolones were prepared using radical alkyne insertions. 6-Substituted phenanthridine and 1-substituted isoquinoline and pyridine derivatives were synthesized assisted by radical isocyanide insertions. Furthermore, a wide scope of quinoline and quinoxaline derivatives were synthesized assisted by domino radical isocyanide/alkyne insertions and isocyanide/cyano insertions respectively. All reactions could be carried out under visible light photoredox catalysis with good to excellent chemical yields.

Key words: photochemistry, radical, alkyne, isocyanide, cyanide, aromatic compounds