Visible-light photocatalyzed oxidative decarboxylation of oxamic acids: a green route to urethanes and ureas

A sustainable metal-free route to urethanes and ureas based on a photocatalyzed oxidative decarboxylation of oxamic acids is described. The reaction includes in situ generation of an isocyanate from the oxamic acid, using an organic dye as a photocatalyst, a hypervalent iodine reagent as an oxidant...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Chemical communications (Cambridge, England) England), 2018, Vol.54 (67), p.9337-934
Hauptverfasser: Pawar, Govind Goroba, Robert, Frédéric, Grau, Etienne, Cramail, Henri, Landais, Yannick
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:A sustainable metal-free route to urethanes and ureas based on a photocatalyzed oxidative decarboxylation of oxamic acids is described. The reaction includes in situ generation of an isocyanate from the oxamic acid, using an organic dye as a photocatalyst, a hypervalent iodine reagent as an oxidant and a light source, which trigger the free-radical decarboxylation. This protocol successfully avoids the isolation, purification and storage of carcinogenic isocyanates and allows elaboration of urethanes and ureas in a one-pot process from commercially available sources. Oxidative decarboxylation of oxamic acids under visible-light irradiation in the presence of alcohols or amines provides urethanes or ureas.
ISSN:1359-7345
1364-548X
DOI:10.1039/c8cc05462b