Visible-Light-Photocatalyzed Reductions of N-Heterocyclic Nitroaryls to Anilines Utilizing Ascorbic Acid Reductant

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http://hdl.handle.net/10138/321993

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Todorov , A , Aikonen , S A A , Muuronen , M & Helaja , J 2019 , ' Visible-Light-Photocatalyzed Reductions of N-Heterocyclic Nitroaryls to Anilines Utilizing Ascorbic Acid Reductant ' , Organic Letters , vol. 21 , no. 10 , pp. 3764–3768 . https://doi.org/10.1021/acs.orglett.9b01205

Title: Visible-Light-Photocatalyzed Reductions of N-Heterocyclic Nitroaryls to Anilines Utilizing Ascorbic Acid Reductant
Author: Todorov, Aleksandar; Aikonen, Santeri Alfred Arttu; Muuronen, Mikko; Helaja, Juho
Contributor: University of Helsinki, Department of Chemistry
University of Helsinki, Department
University of Helsinki, Department of Chemistry
University of Helsinki, Department of Chemistry
Date: 2019-05-17
Language: eng
Number of pages: 5
Belongs to series: Organic Letters
ISSN: 1523-7060
URI: http://hdl.handle.net/10138/321993
Abstract: A photoreductive protocol utilizing [Ru-(bpy)3]2+ photocatalyst, blue light LEDs, and ascorbic acid(AscH2) 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 AscH2, 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.
Subject: 116 Chemical sciences
PHOTOREDOX CATALYSIS
HYDROGENATION
NITROBENZENE
EFFICIENT
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