Photochemical Copper-Catalyzed Reductive Arylation of Nitroarenes with Arylboronic Acids

We report a novel copper-catalyzed reductive arylation of nitroarenes with arylboronic acids under LED light, enabling diarylamine synthesis under mild conditions. This photochemical approach complements traditional methods, leveraging nitroarenes' multifunctionality to activate isopropanol and facilitate arylboronic acid dehydration into reactive arylboroxines. Mechanistic studies highlight arylboroxines as key intermediates and reveal radical pathways supported by detailed experimental evidence. This facile method offers efficient C-N bond formation with broad applications in pharmaceuticals, materials science, and natural product synthesis.

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Publication Details

Journal
Organic Letters
Published
2025-08-21
DOI
https://doi.org/10.1021/acs.orglett.5c03012
Citations
2
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
1.87

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article

Photochemical Copper-Catalyzed Reductive Arylation of Nitroarenes with Arylboronic Acids

Jingyi Huang, Ping Zhang, Yue Wang, Yangyang Liao et al.
2 citations
Organic Letters
Radical Photochemical Reactions
1.87
article

Photochemical Copper-Catalyzed Reductive Arylation of Nitroarenes with Arylboronic Acids

Jingyi Huang, Ping Zhang, Yue Wang, Yangyang Liao, Jinlong Wang, Bin Wang, Li Zhu, Weibing Wu, Chuanzhou Tao
article en
2 citations

Abstract

We report a novel copper-catalyzed reductive arylation of nitroarenes with arylboronic acids under LED light, enabling diarylamine synthesis under mild conditions. This photochemical approach complements traditional methods, leveraging nitroarenes' multifunctionality to activate isopropanol and facilitate arylboronic acid dehydration into reactive arylboroxines. Mechanistic studies highlight arylboroxines as key intermediates and reveal radical pathways supported by detailed experimental evidence. This facile method offers efficient C-N bond formation with broad applications in pharmaceuticals, materials science, and natural product synthesis.

Organic LettersVol. 27(34)
Tongling University (CN), Nanjing University (CN)
Nanjing University, Tongling University, Natural Science Foundation of Anhui Province
Clean water and sanitation
Openalex Percentile: Top 14%
Radical Photochemical Reactions
1.87
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