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Cobalt-Catalyzed Effective Access to Quinoxalines with Insights in Annulation of Terminal Alkynes and <i>o</i>-Phenylenediamines

Huiru Yang, Zheyao Hu, Xin-Chang Li, Ling Wu, Xun‐Xiang Guo

2022Organic Letters24 citationsDOI

Abstract

-phenylenediamines by using a combination of a cobalt catalyst and oxygen as a terminal oxidant is reported. This method shows wide substrate scope and good functional group tolerance and provides a wide range of quinoxalines in good to high yields. The method is demonstrated by its gram-scale and broad potential applications. Furthermore, this protocol serves as a powerful tool for the late-stage functionalization of various complex bioactive molecules and drugs to provide a new class of molecules containing two distinct bioactive molecules directly linked. Detailed mechanistic studies reveal that the current reaction goes through a novel mechanism different from the previously reported glyoxal mechanism.

Topics & Concepts

AnnulationChemistryCombinatorial chemistryCatalysisGlyoxalSubstrate (aquarium)MoleculeFunctional groupCobaltOrganic chemistryOceanographyGeologyPolymerSynthesis and Biological EvaluationCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques
Cobalt-Catalyzed Effective Access to Quinoxalines with Insights in Annulation of Terminal Alkynes and <i>o</i>-Phenylenediamines | Litcius