Temperature-Controlled Switchable Cascade Reactions of Alkyne-Tethered Ketoximes and Cyanobenziodoxolone for Divergent Synthesis Cyano-Featured Isoxazolines and 3 <i>H</i> -Pyrrol-3-ones

Herein, we report a divergent radical cascade reaction of alkyne-tethered ketoximes with a cyanobenziodoxolone (CBX) reagent. Simply by modulating the reaction temperature, this process enables switchable and efficient access to a series of structurally valuable cyano-substituted isoxazolines and 3<i>H</i>-pyrrol-3-ones. Notably, this protocol is characterized by low catalyst loading, broad substrate scope, and operational simplicity. Furthermore, the cyano-containing isoxazolines were obtained with excellent <i>Z</i>-selectivity.

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Publication Details

Journal
Organic Letters
Published
2026-03-02
DOI
https://doi.org/10.1021/acs.orglett.6c00433
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Temperature-Controlled Switchable Cascade Reactions of Alkyne-Tethered Ketoximes and Cyanobenziodoxolone for Divergent Synthesis Cyano-Featured Isoxazolines and 3 H -Pyrrol-3-ones

Jun‐Long Zhan, Lantao Liu, Xingyu Zhang, Gaowei Li et al.
Organic Letters
Catalytic C–H Functionalization Methods
article

Temperature-Controlled Switchable Cascade Reactions of Alkyne-Tethered Ketoximes and Cyanobenziodoxolone for Divergent Synthesis Cyano-Featured Isoxazolines and 3 H -Pyrrol-3-ones

Jun‐Long Zhan, Lantao Liu, Xingyu Zhang, Gaowei Li, Wen-Jun Han, Cai-Jin Liu, Jia-Lin Ma, Lu Li, Xian-Liang Si, Ning-Ning Cao, Jing-Yi Li, Ya Chen
article en

Abstract

Herein, we report a divergent radical cascade reaction of alkyne-tethered ketoximes with a cyanobenziodoxolone (CBX) reagent. Simply by modulating the reaction temperature, this process enables switchable and efficient access to a series of structurally valuable cyano-substituted isoxazolines and 3<i>H</i>-pyrrol-3-ones. Notably, this protocol is characterized by low catalyst loading, broad substrate scope, and operational simplicity. Furthermore, the cyano-containing isoxazolines were obtained with excellent <i>Z</i>-selectivity.

Organic LettersVol. 28(10)
Biomedical Research Networking Center on Neurodegenerative Diseases (ES), Anyang Normal University (CN), Laboratoire de Synthèse Organique (FR), Shanghai Huayi Group (China) (CN), Chemical Synthesis Lab (SG), Shangqiu Normal University (CN)
Openalex Percentile: Top 36%
Catalytic C–H Functionalization Methods
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