Silver-Catalyzed Three-Component Difunctionalization of Alkenes via Radical Pathways: Access to CF3‑Functionalized Alkyl-Substituted 1,4-Naphthoquinone Derivatives

A silver-catalyzed three-component difunctionalization of alkenes by using 2-amino- and 2-hydroxy-1,4-naphthoquinone derivatives as the radical-trapping reagents is reported. Various alkenes and 2-amino- or 2-hydroxy-1,4-naphthoquinones with diverse structures and electronic properties are applied t...

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Bibliographic Details
Published in:Journal of organic chemistry 2019-01, Vol.84 (2), p.1006-1014
Main Authors: Wang, Qijun, Wang, Bo, Deng, Hao, Shangguan, Yu, Lin, Yan, Zhang, Yaqi, Zhang, Zheming, Xiao, Yumei, Guo, Hongchao, Zhang, Cheng
Format: Article
Language:English
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Summary:A silver-catalyzed three-component difunctionalization of alkenes by using 2-amino- and 2-hydroxy-1,4-naphthoquinone derivatives as the radical-trapping reagents is reported. Various alkenes and 2-amino- or 2-hydroxy-1,4-naphthoquinones with diverse structures and electronic properties are applied to the reaction. The methodology provides an alternative method to access CF3-functionalized alkyl-substituted quinone derivatives which are prevalent structures in bioactive molecules. Furthermore, a plausible radical pathway for the reaction is proposed based on results from primary control experiments.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b02997