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Open AccessArticle

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

by Xiubin Liu 1,2,†, Zhixing Qing 1,2,†, Pi Cheng 1,2,*, Xinyu Zheng 1, Jianguo Zeng 1,2 and Hongqi Xie 1,2,*
1
National and Provincial Union Engineering Research Center for the Veterinary Herbal Medicine Resources and Initiative, Hunan Agricultural University, Changsha 410128, China
2
Hunan Co-Innovation Center for Utilization of Botanicals Functional Ingredients, Hunan Agricultural University, Changsha 410128, China
*
Authors to whom correspondence should be addressed.
These authors contributed equally to this work and should be considered joint first authors.
Academic Editor: Derek J. McPhee
Molecules 2016, 21(12), 1690; https://doi.org/10.3390/molecules21121690
Received: 1 November 2016 / Revised: 25 November 2016 / Accepted: 6 December 2016 / Published: 8 December 2016
(This article belongs to the Section Photochemistry)
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. View Full-Text
Keywords: visible light; photoredox catalysis; eosin Y; O-aryl oximes; phenanthridines visible light; photoredox catalysis; eosin Y; O-aryl oximes; phenanthridines
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MDPI and ACS Style

Liu, X.; Qing, Z.; Cheng, P.; Zheng, X.; Zeng, J.; Xie, H. Metal-Free Photoredox Catalyzed Cyclization of O-(2,4-Dinitrophenyl)oximes to Phenanthridines. Molecules 2016, 21, 1690.

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