Palladium-catalyzed synthesis of N-aryloxazolidinones from aryl chlorides

Article abstract of DOI:10.1021/ol034428p

(Matrix presented) An efficient method for intermolecular N-arylation of oxazolidinones using Pd₂dba₃ and various phosphine ligands in the presence of a weak base is reported. The conditions allow the use of cheaper aryl chlorides containing functionalities such as enolizable ketones, amides, etc., which would be incompatible with other coupling methods. The coupling reaction can be used to prepare enantiopure N-aryl β-amino alcohols. Depending on the stereoelectronic nature of the aryl chloride, careful choice of ligand was necessary for the success of these reactions.