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Updated: Jun 23, 2026

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
Published on: April 22, 2016
Photo-triggered Formation of an Amidinyl Radical from O-Nitroveratril Amidoxime and Its Intramolecular Cyclization in
Hidenori Okamura1,2,3, Yui Kaneyama1,2, Kenshin Norizuki1,2
1Institute of Multidisciplinary Research for Advanced Materials, Tohoku University, 2-1-1 Katahira, Aoba-ku, Sendai 980-8577, Japan.
Abstract:
Photochemical reactions compatible with physiological conditions are powerful tools for chemical biology and medicinal chemistry. Herein, we report that 3,4-dimethoxy-o-nitrobenzyl (o-nitroveratril) amidoxime ethers generate amidinyl radicals upon photoirradiation, yielding 6-aminophenanthridines via the intramolecular cyclization of the corresponding biaryl precursors. This photoreaction proceeds under physiologically relevant conditions, specifically in the aqueous buffers, to yield a series of substituted amino-phenanthridines in moderate yields. Mechanistic studies demonstrated that the reaction proceeds through homolytic N-O bond cleavage triggered by the photoexcitation of the o-nitroveratril moiety. Detailed analysis also identified amino-azaspirolactam as a side product, highlighting the bilateral reaction modes of amidoxime-derived radical species. Finally, the photoinduced cyclization was demonstrated within HeLa cells, highlighting its potential for light-induced construction and control of bioactive compounds.
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