Base-Mediated Visible-Light-Driven C–H Arylation of Quinoxalin-2(1<i>H</i>)-Ones in Ethanol

Prior methods for visible-light-driven C–H arylation of quinoxalin-2(1H)-ones relied on external photocatalysts. Herein, we report a photocatalyst-free approach for this arylation. In this approach, β-dicarbonyl iodonium ylides, combined with t-BuOK in ethanol, act as aryl precursors, forming electron donor–acceptor (EDA) complexes. These complexes enhance light absorption, facilitating efficient single electron transfer and aryl radical formation. Consequently, various quinoxalin-2(1H)-ones undergo precise and efficient arylation without external photocatalysts. This protocol exhibits excellent tolerance toward diverse functional groups, with mild reaction conditions and eco-friendly solvents, revealing a high Ecoscale value.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-09-26
DOI
https://doi.org/10.1021/acs.joc.4c01641
Citations
9
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
2.25

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article

Base-Mediated Visible-Light-Driven C–H Arylation of Quinoxalin-2(1H)-Ones in Ethanol

Y. Pan, Xiaobo Yang, Xiubin Bu, Zhen Zhao et al.
9 citations
The Journal of Organic Chemistry
Radical Photochemical Reactions
2.25
article

Base-Mediated Visible-Light-Driven C–H Arylation of Quinoxalin-2(1H)-Ones in Ethanol

Y. Pan, Xiaobo Yang, Xiubin Bu, Zhen Zhao, Guoqing Huang, Luohe Wang, Yunhong Shi
article en
9 citations

Abstract

Prior methods for visible-light-driven C–H arylation of quinoxalin-2(1H)-ones relied on external photocatalysts. Herein, we report a photocatalyst-free approach for this arylation. In this approach, β-dicarbonyl iodonium ylides, combined with t-BuOK in ethanol, act as aryl precursors, forming electron donor–acceptor (EDA) complexes. These complexes enhance light absorption, facilitating efficient single electron transfer and aryl radical formation. Consequently, various quinoxalin-2(1H)-ones undergo precise and efficient arylation without external photocatalysts. This protocol exhibits excellent tolerance toward diverse functional groups, with mild reaction conditions and eco-friendly solvents, revealing a high Ecoscale value.

The Journal of Organic ChemistryVol. 89(19)
Shenyang Normal University (CN), Tsinghua University (CN)
Natural Science Foundation of Shenyang City, Natural Science Foundation of Liaoning Province, Liaoning Revitalization Talents Program
Zero hunger
Openalex Percentile: Top 12%
Radical Photochemical Reactions
2.25
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