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Note | Special issue | Vol 61, No. 1, 2003, pp.505-512
Published online, 19th May, 2003
DOI: 10.3987/COM-03-S7
Copper-catalyzed N-Arylation of 2-Oxazolidinones. An Expeditious Route to Toloxatone

Sandro Cacchi,* Giancarlo Fabrizi, and Antonella Goggiamani

*Department of Chemistry and Technology of Biologically Active Substances, University of Rome “La Sapienza”, P.le A. Moro 5, 00185 Rome

Abstract

3-Aryl-2-oxazolidinones are obtained in excellent yields through the copper-catalyzed N-arylation of 2-oxazolidinones with a variety of aryl iodides. With aryl halides containing both iodo and bromo substituents, a high C-I/C-Br selectivity can be achieved. The procedure has been successfully applied to the preparation of a key intermediate in the synthesis of linezolid and to develop an expeditious route to toloxatone.