Visible Light Photoredox Catalysis in the Synthesis of Phosphonate-Substituted 1,10-Phenanthrolines

Photoredox-catalyzed phosphonylation of bromo-substituted 1,10-phenanthrolines under visible light irradiation was studied. The reaction was shown to proceed under mild conditions with Eosin Y as a photocatalyst in DMSO under blue light irradiation. It is transition-metal-free and affords the target phosphonate-substituted 1,10-phenanthrolines in moderate yields (26-51%) in 22 to 40 h. The rate and selectivity of the reaction depend largely on the position of the bromine atom, as well as on the nature and position of other substituents in the 1,10-phenanthroline core.

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Publication Details

Journal
Molecules
Published
2024-11-25
DOI
https://doi.org/10.3390/molecules29235558
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
0.00

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article

Visible Light Photoredox Catalysis in the Synthesis of Phosphonate-Substituted 1,10-Phenanthrolines

I. P. Beletskaya, Alexei Dmitrievich Averin, Anton S. Abel, Alexander Yu. Mitrofanov et al.
Molecules
Radical Photochemical Reactions
article

Visible Light Photoredox Catalysis in the Synthesis of Phosphonate-Substituted 1,10-Phenanthrolines

I. P. Beletskaya, Alexei Dmitrievich Averin, Anton S. Abel, Alexander Yu. Mitrofanov, Gleb V. Morozkov, Artem A. Troickiy
article en

Abstract

Photoredox-catalyzed phosphonylation of bromo-substituted 1,10-phenanthrolines under visible light irradiation was studied. The reaction was shown to proceed under mild conditions with Eosin Y as a photocatalyst in DMSO under blue light irradiation. It is transition-metal-free and affords the target phosphonate-substituted 1,10-phenanthrolines in moderate yields (26-51%) in 22 to 40 h. The rate and selectivity of the reaction depend largely on the position of the bromine atom, as well as on the nature and position of other substituents in the 1,10-phenanthroline core.

MoleculesVol. 29(23)
Lomonosov Moscow State University (RU), Frumkin Institute of Physical Chemistry and Electrochemistry Russian Academy of Sciences (RU)
Russian Science Foundation
Clean water and sanitation
Openalex Percentile: Top 84%
Radical Photochemical Reactions
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