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...
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Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2018, Vol.54 (67), p.9337-934 |
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Hauptverfasser: | , , , , |
Format: | Artikel |
Sprache: | eng |
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Online-Zugang: | Volltext |
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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. |
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ISSN: | 1359-7345 1364-548X |
DOI: | 10.1039/c8cc05462b |