Litcius/Paper detail

Visible‐Light‐Induced Palladium‐Catalyzed Dehydrogenative Carbonylation of Amines to Oxalamides

Tim Meyer, Jabor Rabeah, Angelika Brückner, Xiao‐Feng Wu

2021Chemistry - A European Journal23 citationsDOI

Abstract

Abstract The palladium‐catalyzed oxidative carbonylation of amines toward the synthesis of oxalamides has been established around 30 years ago and it usually needs the presence of (over)stoichiometric amounts of oxidant. In this work, the first transformation of this type in which the oxidant was replaced by visible light is described. The new approach uses a simple robust Pd complex, which can even be partially recycled. A mechanistic reason is provided and supported by control experiments and EPR studies, showing that Pd I was formed and Pd 0 was the active species. Both nitrogen‐ and the intermediate acyl radical can be detected. Moreover, the formation of hydrogen was confirmed by gas GC.

Topics & Concepts

PalladiumCarbonylationCatalysisChemistryPhotochemistryStoichiometryElectron paramagnetic resonanceHydrogenOxygenOxidative phosphorylationCombinatorial chemistryOrganic chemistryCarbon monoxidePhysicsNuclear magnetic resonanceBiochemistryCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsCarbon dioxide utilization in catalysis