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

doi:10.11944/j.issn.1000-0518.2019.11.190078

Chinese Journal of Applied Chemistry ›› 2019, Vol. 36 ›› Issue (11): 1266-1274.DOI: 10.11944/j.issn.1000-0518.2019.11.190078

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

SHENG Huixiang,YU Jian,WANG Shuowen,XU Zhenhua,TANG Shi()

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

Received:2019-03-25 Accepted:2019-07-16 Published:2019-11-01 Online:2019-11-05
Contact: TANG Shi
Supported by:
Supported by the National Natural Science Foundation of China(No.21662013), and the Research Innovation Program for Graduates of Hunan Province(No.JGY201636).

Abstract

Abstract:

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.

Key words: C—C bond functionalization, 1,1'-azobis(cyanocyclohexane), copper catalysis, benzofuranone, para-quinone methides

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.

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

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