Citation: Wang Bowen, Liu Yuan, Hao Zhifeng, Hou Jiaqi, Li Jianyi, Li Shuting, Pan Sihui, Zeng Minghao, Wang Zhaoyang. Recent Progress in C-C Bond Construction Based on 2(5H)-Furanone[J]. Chinese Journal of Organic Chemistry, ;2018, 38(8): 1872-1884. doi: 10.6023/cjoc201803053 shu

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

Wang Bowen ^a ,
Liu Yuan ^a ,
Hao Zhifeng ^b,, ,
Hou Jiaqi ^a ,
Li Jianyi ^a ,
Li Shuting ^a ,
Pan Sihui ^a ,
Zeng Minghao ^a ,
Wang Zhaoyang ^a,,

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

Corresponding author: Hao Zhifeng, haozhifeng3377@163.com Wang Zhaoyang, wangzy@scnu.edu.cn
Received Date: 30 March 2018
Revised Date: 29 April 2018
Available Online: 14 August 2018
Fund Project: 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)the Applied Science and Technology Research and Development Special Foundation of Guangdong Province 2016B090930004the Undergraduates Innovation Project of South China Normal University 20181442the Guangdong Provincial Science and Technology Project 2017A010103016the Natural Science Foundation of Guangdong Province 2014A030313429the Guangzhou Science and Technology Project Scientific Special 201607010251

Figures(14)

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