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Visible-Light-Photocatalyzed Reductions of N-Heterocyclic Nitroaryls to Anilines Utilizing Ascorbic Acid Reductant
[Image: see text] A photoreductive protocol utilizing [Ru(bpy)(3)](2+) photocatalyst, blue light LEDs, and ascorbic acid (AscH(2)) has been developed to reduce nitro N-heteroaryls to the corresponding anilines. Based on experimental and computational results and previous studies, we propose that the...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2019
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6750875/ https://www.ncbi.nlm.nih.gov/pubmed/31066563 http://dx.doi.org/10.1021/acs.orglett.9b01205 |
Sumario: | [Image: see text] A photoreductive protocol utilizing [Ru(bpy)(3)](2+) photocatalyst, blue light LEDs, and ascorbic acid (AscH(2)) has been developed to reduce nitro N-heteroaryls to the corresponding anilines. Based on experimental and computational results and previous studies, we propose that the reaction proceeds via proton-coupled electron transfer between AscH(2), photocatalyst, and the nitro N-heteroaryl. The method offers a green catalytic procedure to reduce, e.g., 4-/8-nitroquinolines to the corresponding aminoquinolines, substructures present in important antimalarial drugs. |
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