American Chemical Society
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Copper-Catalyzed Three-Component Difunctionalization of Aromatic Alkenes with 2‑Amino-1,4-naphthoquinones and α‑Bromocarboxylates

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journal contribution
posted on 2019-08-08, 19:45 authored by Yu Shangguan, Fazhou Yang, Hao Deng, Hao Liu, Ziyan Liu, Wanyue Zhuang, Chenxi Qiao, Aizheng Wang, Yumei Xiao, Cheng Zhang
A copper-catalyzed three-component difunctionalization of aromatic alkenes to access 1,4-naphthoquinone derivatives with diverse structures is described. Experiments show that the difunctionalization reaction is accompanied by ester exchange reaction with the solvent. In this method, α-bromocarboxylates are used as radical precursors and 2-amino-1,4-naphthoquinones as radical trapping reagents. The substrate scope is broad because various aromatic alkenes, 2-amino-1,4-naphthoquinones, and α-bromocarboxylates are employed in the reaction, and corresponding products are obtained in moderate to good yields.