Visible‐Light‐Promoted Intermolecular Oxidative Dearomatization of β‐Naphthols with <i>N</i>‐Hydroxycarbamates

Yuan‐Zheng Cheng, Kai Zhou, Min Zhu, L.-P. Li, Xiǎo Zhang, Shu‐Li You

Chemistry - A European Journal · 2018 · 28 citations · 68 references

Concepts

Abstract

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 Cs 2 CO 3 . This transformation simultaneously provides an attractive and synthetically useful approach to access the aminative dearomatization compounds.

References

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