Visible-Light-Promoted Cascade Radical Trifluoromethylation/Cyclization for the Synthesis of Trifluoromethylated Tricyclic Quinoxalinonyl Compounds

Tricyclic quinoxalinonyl compounds represent an important class of tricyclic fused <i>N</i>-heterocyclic systems widely distributed in pharmaceutical agents and biologically active molecules. Herein, we described a visible-light-induced radical trifluoromethylation/cyclization reaction using cost-effective and readily available CF<sub>3</sub>Br as the trifluoromethyl source. This strategy enables, for the first time, the efficient construction of a series of trifluoromethylated tricyclic quinoxalinonyl compounds from <i>N</i>-(isopentenyl)quinoxalin-2(1<i>H</i>)-ones and <i>N</i>-homoallylquinoxalin-2(1<i>H</i>)-ones via radical trifluoromethylation/cyclization. The method features mild reaction conditions and excellent functional group compatibility and can be extended to various fluoroalkyl reagents such as C<sub>6</sub>F<sub>13</sub>Br and C<sub>8</sub>F<sub>17</sub>Br, providing a mild and efficient synthetic approach for introducing diverse fluoroalkyl groups to organic compounds.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2026-01-06
DOI
https://doi.org/10.1021/acs.joc.5c02647
Citations
1
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
27.80
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article

Visible-Light-Promoted Cascade Radical Trifluoromethylation/Cyclization for the Synthesis of Trifluoromethylated Tricyclic Quinoxalinonyl Compounds

Yulai Hu, Zhoubin Deng, Zhang Bosheng, JunJiao Wang et al.
1 citations
The Journal of Organic Chemistry
Fluorine in Organic Chemistry
27.80
article

Visible-Light-Promoted Cascade Radical Trifluoromethylation/Cyclization for the Synthesis of Trifluoromethylated Tricyclic Quinoxalinonyl Compounds

Yulai Hu, Zhoubin Deng, Zhang Bosheng, JunJiao Wang, Ke‐Hu Wang, Yuyu Lv, Danfeng Huang, Zhijun Zhu
article en
1 citations

Abstract

Tricyclic quinoxalinonyl compounds represent an important class of tricyclic fused <i>N</i>-heterocyclic systems widely distributed in pharmaceutical agents and biologically active molecules. Herein, we described a visible-light-induced radical trifluoromethylation/cyclization reaction using cost-effective and readily available CF<sub>3</sub>Br as the trifluoromethyl source. This strategy enables, for the first time, the efficient construction of a series of trifluoromethylated tricyclic quinoxalinonyl compounds from <i>N</i>-(isopentenyl)quinoxalin-2(1<i>H</i>)-ones and <i>N</i>-homoallylquinoxalin-2(1<i>H</i>)-ones via radical trifluoromethylation/cyclization. The method features mild reaction conditions and excellent functional group compatibility and can be extended to various fluoroalkyl reagents such as C<sub>6</sub>F<sub>13</sub>Br and C<sub>8</sub>F<sub>17</sub>Br, providing a mild and efficient synthetic approach for introducing diverse fluoroalkyl groups to organic compounds.

The Journal of Organic ChemistryVol. 91(2)
State Key Laboratory of Chemical Engineering (CN), Northwest Normal University (CN), Lanzhou University (CN)
Openalex Percentile: Top 2%
Fluorine in Organic Chemistry
27.80
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