Transition metal-free visible light-mediated photocatalytic aerobic oxidative synthesis of N-heterocycles using molecular oxygen as an oxidant

•Transition metal-free visible light-mediated method for the construction of various N-heterocycles at room temperature.•4CzIPN was used as photocatalyst with molecular oxygen as terminal oxidant.•This photocatalytic system exhibits good functional group tolerance.•Biologically active natural produc...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Molecular catalysis 2024-09, Vol.566, p.114432, Article 114432
Hauptverfasser: Hu, Yongke, Tian, Hongyou, Cao, Haotian, Li, Jin, Li, Shaozhong, Li, Huaju, Li, Yanxing, Shen, Gulou, Chen, Lei
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:•Transition metal-free visible light-mediated method for the construction of various N-heterocycles at room temperature.•4CzIPN was used as photocatalyst with molecular oxygen as terminal oxidant.•This photocatalytic system exhibits good functional group tolerance.•Biologically active natural product Schizocommunin and its derivatives were successfully synthesized.•A plausible reaction mechanism involving a radical process was proposed. A novel, transition metal-free visible light-mediated method for the construction of N-heterocycles from easily available aldehydes and o-substituted anilines in the presence of 4CzIPN under oxygen atmosphere has been developed. This photocatalytic system is a sustainable and atom-economical methodology that avoids toxic chemical additives and transition metals under ambient conditions. A variety of functionalized nitrogenous heterocyclic compounds are obtained in good to excellent yields. Notably, the biologically active natural product Schizocommunin and its derivatives are successfully synthesized, which might indicate this protocol has more applications in the future. In addition, a plausible reaction mechanism involving a radical process has been proposed based on control experiments and mechanism exploration, and further applications of this catalytic system are under way in our laboratory. A novel, transition metal-free visible light-mediated method for the construction of N-heterocycles from easily available aldehydes and o-substituted anilines in the presence of 4CzIPN under oxygen atmosphere has been developed. [Display omitted]
ISSN:2468-8231
2468-8231
DOI:10.1016/j.mcat.2024.114432