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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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
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author Todorov, Aleksandar R.
Aikonen, Santeri
Muuronen, Mikko
Helaja, Juho
author_facet Todorov, Aleksandar R.
Aikonen, Santeri
Muuronen, Mikko
Helaja, Juho
author_sort Todorov, Aleksandar R.
collection PubMed
description [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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spelling pubmed-67508752019-09-19 Visible-Light-Photocatalyzed Reductions of N-Heterocyclic Nitroaryls to Anilines Utilizing Ascorbic Acid Reductant Todorov, Aleksandar R. Aikonen, Santeri Muuronen, Mikko Helaja, Juho Org Lett [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. American Chemical Society 2019-05-08 2019-05-17 /pmc/articles/PMC6750875/ /pubmed/31066563 http://dx.doi.org/10.1021/acs.orglett.9b01205 Text en Copyright © 2019 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Todorov, Aleksandar R.
Aikonen, Santeri
Muuronen, Mikko
Helaja, Juho
Visible-Light-Photocatalyzed Reductions of N-Heterocyclic Nitroaryls to Anilines Utilizing Ascorbic Acid Reductant
title Visible-Light-Photocatalyzed Reductions of N-Heterocyclic Nitroaryls to Anilines Utilizing Ascorbic Acid Reductant
title_full Visible-Light-Photocatalyzed Reductions of N-Heterocyclic Nitroaryls to Anilines Utilizing Ascorbic Acid Reductant
title_fullStr Visible-Light-Photocatalyzed Reductions of N-Heterocyclic Nitroaryls to Anilines Utilizing Ascorbic Acid Reductant
title_full_unstemmed Visible-Light-Photocatalyzed Reductions of N-Heterocyclic Nitroaryls to Anilines Utilizing Ascorbic Acid Reductant
title_short Visible-Light-Photocatalyzed Reductions of N-Heterocyclic Nitroaryls to Anilines Utilizing Ascorbic Acid Reductant
title_sort visible-light-photocatalyzed reductions of n-heterocyclic nitroaryls to anilines utilizing ascorbic acid reductant
url 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
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