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
Hauptverfasser: Pawar, Govind Goroba, Robert, Frédéric, Grau, Etienne, Cramail, Henri, Landais, Yannick
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container_issue 67
container_start_page 9337
container_title Chemical communications (Cambridge, England)
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creator Pawar, Govind Goroba
Robert, Frédéric
Grau, Etienne
Cramail, Henri
Landais, Yannick
description 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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source Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
subjects Carcinogens
Chemical Sciences
Decarboxylation
Iodine
Isocyanates
Organic chemistry
Oxamic acids
Polymers
Reagents
Ureas
Urethanes
title Visible-light photocatalyzed oxidative decarboxylation of oxamic acids: a green route to urethanes and ureas
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