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

被引:0
|
作者
Pan, Yitong [1 ]
Wang, Luohe [1 ]
Shi, Yunhong [1 ]
Huang, Guoqing [1 ]
Bu, Xiubin [1 ]
Yang, Xiaobo [1 ,2 ]
Zhao, Zhen [1 ]
机构
[1] Shenyang Normal Univ, Inst Catalysis Energy & Environm, Coll Chem & Chem Engn, Shenyang 110034, Peoples R China
[2] Tsinghua Univ, Dept Chem, Key Lab Bioorgan Phosphorus Chem & Chem Biol, Minist Educ, Beijing 100084, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 19期
关键词
METAL-FREE; DESIGN; PHOTOCATALYST; CHEMISTRY; ALKENES; ACIDS;
D O I
10.1021/acs.joc.4c01641
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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, beta-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.
引用
收藏
页码:14217 / 14227
页数:11
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