(KOBu)-Bu-t-promoted C3-homocoupling of quinoxalinones through single electron transfer from an sp(2) carbanion intermediate
- Authors
- Kwon, Na Yeon; Mishra, Neeraj Kumar; Park, Jung Su; Woo, Sang Kook; Ghosh, Prithwish; Kim, In Su
- Issue Date
- Jun-2022
- Publisher
- ROYAL SOC CHEMISTRY
- Citation
- CHEMICAL COMMUNICATIONS, v.58, no.50, pp 7078 - 7081
- Pages
- 4
- Journal Title
- CHEMICAL COMMUNICATIONS
- Volume
- 58
- Number
- 50
- Start Page
- 7078
- End Page
- 7081
- URI
- https://scholarworks.sookmyung.ac.kr/handle/2020.sw.sookmyung/152733
- DOI
- 10.1039/d2cc02636h
- ISSN
- 1359-7345
1364-548X
- Abstract
- The C3-selective homodimerization of quinoxalinones is described. A C3-sp(2) carbanion species generated through deprotonation of quinoxalinone using potassium tert-butoxide ((KOBu)-Bu-t) transfers an electron (single electron transfer mechanism) to a second quinoxalinone, affording a radical-anion intermediate. The radical scavenging and electron paramagnetic resonance (EPR) experiments support the plausible radical reaction pathway. A mild reaction temperature and a short reaction time were attained under cost-effective conditions, which reveal the amenability of this protocol to pharmaceutical and chemical industries.
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