Photoinduced Cross-Coupling Reactions of Diazoalkanes via a Selective Denitrogenation/Cyclization/Addition Cascade for Diversity-Oriented Synthesis of <i>N</i>-Acyl Pyrazolines

Herein, we present a coupling reaction of two-component diazoalkanes via a selective denitrogenation/cyclization/addition cascade under visible light irradiation for the diversity-oriented synthesis of <i>N</i>-acyl pyrazolines, using readily available diazoesters and diazoketones as substrates. The protocol features conditions that are free of photocatalysts, exhibit atomic economy, allow for simple operation, and demonstrate excellent chemoselectivity. These results, which suggest a reduction in the proliferation of T cells, indicate that <i>N</i>-acyl pyrazolines might have anti-inflammatory and immune-regulatory potential.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-09-25
DOI
https://doi.org/10.1021/acs.joc.5c01544
Primary Topic
Cyclopropane Reaction Mechanisms
Type
article
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article

Photoinduced Cross-Coupling Reactions of Diazoalkanes via a Selective Denitrogenation/Cyclization/Addition Cascade for Diversity-Oriented Synthesis of N-Acyl Pyrazolines

Chenggui Wu, Jing Li, Fengya He, Fang Li et al.
The Journal of Organic Chemistry
Cyclopropane Reaction Mechanisms
article

Photoinduced Cross-Coupling Reactions of Diazoalkanes via a Selective Denitrogenation/Cyclization/Addition Cascade for Diversity-Oriented Synthesis of N-Acyl Pyrazolines

Chenggui Wu, Jing Li, Fengya He, Fang Li, Qinglin Li, Yiwei Xu, Wenyong Li, Jing Zhu
article en

Abstract

Herein, we present a coupling reaction of two-component diazoalkanes via a selective denitrogenation/cyclization/addition cascade under visible light irradiation for the diversity-oriented synthesis of <i>N</i>-acyl pyrazolines, using readily available diazoesters and diazoketones as substrates. The protocol features conditions that are free of photocatalysts, exhibit atomic economy, allow for simple operation, and demonstrate excellent chemoselectivity. These results, which suggest a reduction in the proliferation of T cells, indicate that <i>N</i>-acyl pyrazolines might have anti-inflammatory and immune-regulatory potential.

The Journal of Organic ChemistryVol. 90(39)
Fuyang Normal University (CN), Ministry of Education of the People's Republic of China (CN), Anhui University of Traditional Chinese Medicine (CN), Center for Human Reproduction (US)
Openalex Percentile: Top 80%
Cyclopropane Reaction Mechanisms
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Photoinduced Cross-Coupling Reactions of Diazoalkanes via a Selective Denitrogenation/Cyclization/Addition Cascade for Diversity-Oriented Synthesis of <i>N</i>-Acyl Pyrazolines — Chenggui Wu, Jing Li, et al. · The Journal of Organic Chemistry (2025) | TGRS Research Map | TGRS