Visible-Light-Promoted Intermolecular Oxidative Dearomatization of ß-Naphthols with N-Hydroxycarbamates.

An intermolecular oxidative dearomatization of ß-naphthols with N-hydroxycarbamates promoted by visible light was realized by means of photogenerated ß-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.