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

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posted on 28.12.2018, 00:00 authored by Qijun Wang, Bo Wang, Hao Deng, Yu Shangguan, Yan Lin, Yaqi Zhang, Zheming Zhang, Yumei Xiao, Hongchao Guo, Cheng Zhang
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.