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.
Authors
- Y. Pan (ORCID: https://orcid.org/0000-0002-4110-7299)
- Xiaobo Yang (ORCID: https://orcid.org/0000-0003-0684-8419)
- Xiubin Bu (ORCID: https://orcid.org/0009-0006-0364-2940)
- Zhen Zhao (ORCID: https://orcid.org/0000-0003-0044-5512)
- Guoqing Huang (ORCID: https://orcid.org/0009-0003-1321-1050)
- Luohe Wang
- Yunhong Shi
Institutions
- Shenyang Normal University (CN)
- Tsinghua University (CN)
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
Funders
- Natural Science Foundation of Shenyang City
- Natural Science Foundation of Liaoning Province
- Liaoning Revitalization Talents Program