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Visible‐Light‐Promoted Intermolecular Oxidative Dearomatization of β‐Naphthols with N ‐Hydroxycarbamates
Author(s) -
Cheng YuanZheng,
Zhou Kai,
Zhu Min,
Li LaAoChuan,
Zhang Xiao,
You ShuLi
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201803149
Subject(s) - stereocenter , intermolecular force , yield (engineering) , chemistry , photochemistry , oxidative phosphorylation , oxidative coupling of methane , medicinal chemistry , organic chemistry , enantioselective synthesis , molecule , materials science , catalysis , biochemistry , metallurgy
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 Cs 2 CO 3 . This transformation simultaneously provides an attractive and synthetically useful approach to access the aminative dearomatization compounds.