4.6 Article

Metal-Free Photoredox Catalyzed Cyclization of O-(2,4-Dinitrophenyl)oximes to Phenanthridines

Journal

MOLECULES
Volume 21, Issue 12, Pages -

Publisher

MDPI
DOI: 10.3390/molecules21121690

Keywords

visible light; photoredox catalysis; eosin Y; O-aryl oximes; phenanthridines

Funding

  1. National Natural Science Foundation of China [31402109]
  2. Scientific Research Fund of Hunan Provincial Education Department [14C0564]
  3. Postgraduate Research and Innovation Project of Hunan Province [CX2014B302]

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A metal-free visible-light photoredox-catalyzed intermolecular cyclization reaction of O-2,4-dinitrophenyl oximes to phenanthridines was developed. In this study, the organic dye eosin Y and i-Pr2NEt were used as photocatalyst and terminal reductant, respectively. The oxime substrates were transformed into iminyl radical intermediates by single-electron reduction, which then underwent intermolecular homolytic aromatic substitution (HAS) reactions to give phenanthridine derivatives.

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