Synthesis 2007(15): 2297-2306  
DOI: 10.1055/s-2007-983782
© Georg Thieme Verlag Stuttgart · New York

A Domino Copper-Catalyzed C-N and C-O Cross-Coupling for the Conversion­ of Primary Amides into Oxazoles

Kerstin Schuh (née Müller), Frank Glorius*
Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Straße, 35032 Marburg, Germany
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Publication History

Received 9 March 2007
Publication Date:
12 July 2007 (online)


A variety of oxazoles can efficiently be prepared, in a single step and in good yield, from primary amides and 1,2-dihaloalkenes using copper-catalysis. This new method allows the re­gioselective formation of a range of substituted oxazoles. The required 1,2-dihaloalkenes can prepared by simple treatment of alkynes with elemental bromine or iodine.


Parameters screened: Ligands: DMEDA (optimal), rac-1,2-diaminocyclohexane (lower conversion, more side products), phenanthroline (no reaction); bases: K2CO3 (optimal), K3PO4 (lower conversion, more side products), Cs2CO3 (lower conversion), Et3N and NaOAc (no reaction). Reaction temperature: <110 °C conversion was found to be incomplete; solvents: toluene (optimal), chlorobenzene (lower conversion), t-BuOH, dioxane (much lower conversion), DMF (no conversion).