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.landais
u‐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.
see article for more examples
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
