Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (8): 1872-1884.DOI: 10.6023/cjoc201803053 Previous Articles     Next Articles



王柏文a, 刘园a, 郝志峰b, 侯佳琦a, 李健怡a, 李舒婷a, 潘思慧a, 曾铭豪a, 汪朝阳a   

  1. a 华南师范大学化学与环境学院 教育部环境理论化学重点实验室 广州 510006;
    b 广东工业大学轻工化工学院 广州 510006
  • 收稿日期:2018-03-30 修回日期:2018-04-29 发布日期:2018-05-14
  • 通讯作者: 郝志峰, 汪朝阳;
  • 基金资助:


Recent Progress in C-C Bond Construction Based on 2(5H)-Furanone

Wang Bowena, Liu Yuana, Hao Zhifengb, Hou Jiaqia, Li Jianyia, Li Shutinga, Pan Sihuia, Zeng Minghaoa, Wang Zhaoyanga   

  1. a School of Chemistry and Environment, South China Normal University, Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou 510006;
    b School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou 510006
  • Received:2018-03-30 Revised:2018-04-29 Published:2018-05-14
  • Contact: 10.6023/cjoc201803053;
  • Supported by:

    Project supported by the Undergraduates Innovation Project of South China Normal University (No. 20181442), the Natural Science Foundation of Guangdong Province (No. 2014A030313429), the Guangzhou Science and Technology Project Scientific Special (No. 201607010251), the Applied Science and Technology Research and Development Special Foundation of Guangdong Province (No. 2016B090930004) and the Guangdong Provincial Science and Technology Project (No. 2017A010103016).

2(5H)-Furanone contains several reaction points, and its structure unit exists in a number of nature products, which makes the researches on the derivatizations of 2(5H)-furanone important. Some 2(5H)-furanone compounds, such as 3-(or 4-) halo-2(5H)-furanone, 5-nonsubstitued 2(5H)-furanone, 4-hydroxy-2(5H)-furanone and their derivatives, can react with organometallic reagents, alkyl halides, organoboron compounds, unsaturated hydrocarbons and unsaturated C=X (X=O, N) compounds, forming C-C bond at 3-, or 4-, or 5-position of 2(5H)-furanone, respectively. According to the different types of reagents, the C-C bond formation reactions based on 2(5H)-furanone synthons are reviewed, and their recent progress in organic synthesis methodology and application of bioactive compounds is summarized. In the future, it is important to make the 2(5H)-furanone C-C bond formation reaction more greener and efficiently used in polycyclization reaction.

Key words: 2(5H)-furanone, C-C bond formation, metal-catalyzed coupling reaction, organocatalytic vinylogous reaction, polycyclization reaction