Construction of 3‑Oxazolin-5-one via Visible Light-Induced Nondecarboxylative Coupling and Sequential Reactions

3-Oxazolin-5-ones are precursors of nitrile ylides and represent valuable 1,3-dipoles for constructing cyclic imines or pyrrole compounds. Harnessing the power of photocatalysis, we accomplished a straightforward synthesis of 3-oxazolin-5-ones from redox-active esters and secondary nitro compounds....

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2023-03, Vol.25 (12), p.2098-2102
Hauptverfasser: Ma, Shanshan, Cao, Haoying, Gao, Rongwan, Feng, Yanhong, Guo, Yawen, Guan, Wei, Duan, Xinfang, Jiao, Peng
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:3-Oxazolin-5-ones are precursors of nitrile ylides and represent valuable 1,3-dipoles for constructing cyclic imines or pyrrole compounds. Harnessing the power of photocatalysis, we accomplished a straightforward synthesis of 3-oxazolin-5-ones from redox-active esters and secondary nitro compounds. Visible light-induced nondecarboxylative coupling of a redox-active ester, nitro aldol condensation, and subsequent visible light-induced N-oxide deoxygenation were accomplished within 2 h. The reaction mechanism was supported by experimental data and DFT calculations.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c00469