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Visible-Light-Promoted Intermolecular Oxidative Dearomatization of β-Naphthols with N-Hydroxycarbamates
Yuan-Zheng Cheng1, Kai Zhou1, Min Zhu1,2
1Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, P. R. China.
Abstract:
An intermolecular oxidative dearomatization of β-naphthols with N-hydroxycarbamates promoted by visible light was realized by means of photogenerated β-naphthol radical cation intermediates. With a commercially available organic dye, the naphthalenones bearing a fully substituted stereogenic center were obtained with up to 92 % yield under aerobic conditions (26 examples). In addition, the rearrangement of C-O coupling products to C-N coupling compounds could be achieved merely in the presence of Cs2 CO3 . This transformation simultaneously provides an attractive and synthetically useful approach to access the aminative dearomatization compounds.
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