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

Govind Goroba Pawar , Frédéric Robert (1) , Etienne Grau (2) , Henri Cramail (2) , Yannick Landais (1)

1 ISM - Institut des Sciences Moléculaires
2 LCPO - Laboratoire de Chimie des Polymères Organiques

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.

Domaines: Polymères; Chimie organique; Chimie

Govind Goroba Pawar, Frédéric Robert, Etienne Grau, Henri Cramail, Yannick Landais. Visible-light photocatalyzed oxidative decarboxylation of oxamic acids: a green route to urethanes and ureas. Chemical Communications, 2018, 54 (67), pp.9337 - 9340. ⟨10.1039/c8cc05462b⟩. ⟨hal-01917923⟩