title: Synthesis of Allenamides by Copper-Catalyzed Coupling of Propargylic Bromides and Nitrogen Nucleophiles.
abstract: An efficient and general synthesis of allenamides derived from oxazolidinones and hydantoins is reported. Upon activation with a combination of a copper catalyst and a 2,2'-bipyridine derivative in the presence of an inorganic base, propargylic bromides were found to be suitable reagents for the direct allenylation of nitrogen nucleophiles by a formal copper-catalyzed S(N)2' reaction. Besides the availability of the starting materials, notable features of this route to allenamides are its mild reaction conditions, the reaction being performed at room temperature in most cases, and its applicability to the preparation of mono-, di-, as well as trisubstituted allenamides.
authors.affiliation: Laboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques, Université libre de Bruxelles (ULB) , Avenue F. D. Roosevelt 50, CP160/06, 1050 Brussels, Belgium.
authors.forename: Charles S
authors.initials: CS
authors.lastname: Demmer
authors.affiliation: Laboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques, Université libre de Bruxelles (ULB) , Avenue F. D. Roosevelt 50, CP160/06, 1050 Brussels, Belgium.
authors.forename: Emeline
authors.initials: E
authors.lastname: Benoit
authors.affiliation: Laboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques, Université libre de Bruxelles (ULB) , Avenue F. D. Roosevelt 50, CP160/06, 1050 Brussels, Belgium.
authors.forename: Gwilherm
authors.initials: G
authors.lastname: Evano
mesh_terms: D015082:2,2'-Dipyridyl / Q000737:chemistry; D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D023303:Oxazolidinones / Q000737:chemistry*; D010293:Pargyline / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D000577:Amides; D023303:Oxazolidinones; D015082:2,2'-Dipyridyl; D003300:Copper; D010293:Pargyline; C458239:propargyl bromide; D009584:Nitrogen