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Updated: Sep 20, 2025
![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)
Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
KOBu-promoted C3-homocoupling of quinoxalinones through single electron transfer from an sp2 carbanion intermediate
Na Yeon Kwon1, Neeraj Kumar Mishra1, Jung Su Park2
1School of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of Korea. insukim@skku.edu.
Abstract:
The C3-selective homodimerization of quinoxalinones is described. A C3-sp2 carbanion species generated through deprotonation of quinoxalinone using potassium tert-butoxide (KOBu) 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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