Copper-Catalyzed, Regioselective, Unsymmetrical Homocoupling of Quinoxalin-2(1 H)-ones to Form C-N Homodimers

Qiming Yang; Yueyue Hu; Xiangtao Kong; Yi-Zhu Lei

doi:10.1021/acs.joc.3c00544

Copper-Catalyzed, Regioselective, Unsymmetrical Homocoupling of Quinoxalin-2(1 H)-ones to Form C-N Homodimers

J Org Chem. 2023 Oct 20;88(20):14274-14282. doi: 10.1021/acs.joc.3c00544. Epub 2023 Sep 29.

Authors

Qiming Yang¹, Yueyue Hu¹, Xiangtao Kong², Yi-Zhu Lei¹

Affiliations

¹ Guizhou Provincial Key Laboratory of Coal Clean Utilization, School of Chemistry and Materials Engineering, Liupanshui Normal University, Liupanshui, Guizhou 553004, PR China.
² Henan Key Laboratory of New Optoelectronic Functional Materials, College of Chemistry and Chemical Engineering, Anyang Normal University, Anyang 455000, China.

PMID: 37774417
DOI: 10.1021/acs.joc.3c00544

Abstract

An environmentally benign and efficient method for the synthesis of unsymmetrical diquinoxalin-2(1H)-ones with potential axial chirality via inexpensive copper-catalyzed, low-toxicity, and stable PIFA oxidation, rarely assisted by PhSeSePh, regioselective homocoupling of quinoxalin-2(1H)-ones under mild conditions is developed. This practical scheme is compatible with a variety of functional groups and allows the preparation of functionalized unsymmetrical dimeric quinoxalin-2(1H)-ones from readily available and safe starting materials, providing new ideas for the sustainable development of methodological studies of quinoxalin-2(1H)-ones.