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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...

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Detalles Bibliográficos
Autores principales: Todorov, Aleksandar R., Aikonen, Santeri, Muuronen, Mikko, Helaja, Juho
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
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
Descripción
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.