Para ‐Selective C─H Amination of Benzenepropanamides via Photocatalytic N ‐Centered Radical‐Mediated Dearomatization

We report a photocatalytic strategy for constructing para ‐aminobenzenepropanamide scaffolds. This method employs oxime‐ester‐based diamination reagents as dual‐radical precursors to generate imino and amidyl radicals. The key step involves N ‐centered radical‐mediated intramolecular dearomatization, forming the cyclohexadienyl radical (CHDR) intermediate. This protocol features mild reaction conditions and broad functional group tolerance. Furthermore, this method achieves selectivity that is not affected by the stereochemical or electronic properties of the benzene ring, thereby enabling the efficient synthesis of 4‐aminobenzoylamide.

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Publication Details

Journal
Advanced Synthesis & Catalysis
Published
2026-10-28
DOI
https://doi.org/10.1002/adsc.70851
Primary Topic
Radical Photochemical Reactions
Type
article
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article

Para ‐Selective C─H Amination of Benzenepropanamides via Photocatalytic N ‐Centered Radical‐Mediated Dearomatization

Lulu Qin, Peng‐Ju Xia, Yu Jian Lv, Shu‐Hui Li et al.
Advanced Synthesis & Catalysis
Radical Photochemical Reactions
article

Para ‐Selective C─H Amination of Benzenepropanamides via Photocatalytic N ‐Centered Radical‐Mediated Dearomatization

Lulu Qin, Peng‐Ju Xia, Yu Jian Lv, Shu‐Hui Li, Di-Jing Luo, Yu Zheng, Zhipeng Ye, Li‐Ning Chen, Dan‐Na Chen
article en

Abstract

We report a photocatalytic strategy for constructing para ‐aminobenzenepropanamide scaffolds. This method employs oxime‐ester‐based diamination reagents as dual‐radical precursors to generate imino and amidyl radicals. The key step involves N ‐centered radical‐mediated intramolecular dearomatization, forming the cyclohexadienyl radical (CHDR) intermediate. This protocol features mild reaction conditions and broad functional group tolerance. Furthermore, this method achieves selectivity that is not affected by the stereochemical or electronic properties of the benzene ring, thereby enabling the efficient synthesis of 4‐aminobenzoylamide.

Advanced Synthesis & CatalysisVol. 368(21)
Central South University (CN), Hainan Normal University (CN), Guangxi Normal University (CN)
Openalex Percentile: Top 26%
Radical Photochemical Reactions
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