Iron-Catalyzed Oxidative Decarboxylation of Oxamic Acids: A Safe and Efficient Photochemical Route to Urethanes
Gülbin Kurtay, Jonathan Lusseau, Frédéric Robert, Yannick Landais*
*University of Bordeaux, CNRS, Bordeaux INP, ISM, UMR 5255, F-33400, Talence, France, Email: yannick.landaisu‐bordeaux.fr
G. Kurtay, J. Lusseau, F. Robert, Y. Landais, Synlett, 2024, 35, 342-346.
DOI: 10.1055/a-2131-3368
Abstract
A photocatalyzed oxidative decarboxylation of oxamic acids enables a facile one-pot synthesis of urethanes. The process involves the formation of an isocyanate in situ from an oxamic acid under blue-light irradiation in the presence of ferrocene as a photocatalyst, 2-picolinic acid as a ligand, and potassium bromate as an oxidant. The method avoids the need for handling carcinogenic isocyanates.
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Note
Phenols and aniline derivatives do effectively work. We have reported another paper more recently where we show that N-aryloxamic acids are indeed converted by our Fe-photocatalyzed LMCT process into urethanes. See : Copper-mediated Synthesis of N-Aryl-oxamic Acids. M. Badufle, F. Robert, Y. Landais, Chem. Eur. J. 2024, 30, e202402298. DOI: 10.1002/chem.202402298
Yannick Landais, October 10, 2024
Key Words
carbamates, photochemistry, potassium bromate, decarboxylation
ID: J72-Y2024