Citation: SHENG Huixiang, YU Jian, WANG Shuowen, XU Zhenhua, TANG Shi. Copper-Catalyzed Three-Component Synthesis of Benzofuran-2-one from para-Quinone Methides/Azo Reagent/H₂O[J]. Chinese Journal of Applied Chemistry, ;2019, 36(11): 1266-1274. doi: 10.11944/j.issn.1000-0518.2019.11.190078 shu

Copper-Catalyzed Three-Component Synthesis of Benzofuran-2-one from para-Quinone Methides/Azo Reagent/H₂O

Hunan Engineering Laboratory for Analyse and Drugs Development of Ethnomedicine in Wuling ountains, College of Chemistry and Chemical Engineering Jishou University, Hunan, Jishou 416000, China

Corresponding author: TANG Shi, stang@jsu.edu.cn
Received Date: 25 March 2019
Revised Date: 28 May 2019
Accepted Date: 16 July 2019

Fund Project: the National Natural Science Foundation of China 21662013the Research Innovation Program for Graduates of Hunan Province JGY201636Supported by the National Natural Science Foundation of China(No.21662013), and the Research Innovation Program for Graduates of Hunan Province(No.JGY201636)

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A new and efficient method for the synthesis of potentially biologically active cyano-containing benzofuran-2-one derivatives has been developed. In the presence of low-cost CuI and zinc powder, the three-component reactions of para-quinone methides with 1, 1-azobis(cyclohexanecarbonitrile) and H₂O proceed smoothly through radical cascades, including 1, 6-conjugate addition/aromatization, inert C(aryl)-C(t-butyl) bond cleavage and downstream cyano-insertion/cyclization/hydrolysis, which leads to a series of cyano-containing benzofuran-2-ones. This method offers a simple and efficient way for the synthesis of cyano-containing benzofuranone derivatives, as well as a new idea for the high-value application of para-quinone methides.
- C-C bond functionalization,
- 1, 1'-azobis(cyanocyclohexane),
- copper catalysis,
- benzofuranone,
- para-quinone methides
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Copper-Catalyzed Three-Component Synthesis of Benzofuran-2-one from para-Quinone Methides/Azo Reagent/H2O

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通讯作者: 陈斌, bchen63@163.com

Copper-Catalyzed Three-Component Synthesis of Benzofuran-2-one from para-Quinone Methides/Azo Reagent/H₂O