title: Copper(II)-catalyzed amidations of alkynyl bromides as a general synthesis of ynamides and Z-enamides. An intramolecular amidation for the synthesis of macrocyclic ynamides.
abstract: A general and efficient method for the coupling of a wide range of amides with alkynyl bromides is described here. This novel amidation reaction involves a catalytic protocol using copper(II) sulfate-pentahydrate and 1,10-phenanthroline to direct the sp-C-N bond formation, leading to a structurally diverse array of ynamides including macrocyclic ynamides via an intramolecular amidation. Given the surging interest in ynamide chemistry, this atom economical synthesis of ynamides should invoke further attention from the synthetic organic community.
authors.affiliation: Division of Pharmaceutical Sciences, 777 Highland Avenue, University of Wisconsin, Madison, Wisconsin 53705, USA.
authors.forename: Xuejun
authors.initials: X
authors.lastname: Zhang
authors.forename: Yanshi
authors.initials: Y
authors.lastname: Zhang
authors.forename: Jian
authors.initials: J
authors.lastname: Huang
authors.forename: Richard P
authors.initials: RP
authors.lastname: Hsung
authors.forename: Kimberly C M
authors.initials: KC
authors.lastname: Kurtz
authors.forename: Jossian
authors.initials: J
authors.lastname: Oppenheimer
authors.forename: Matthew E
authors.initials: ME
authors.lastname: Petersen
authors.forename: Irina K
authors.initials: IK
authors.lastname: Sagamanova
authors.forename: Lichun
authors.initials: L
authors.lastname: Shen
authors.forename: Michael R
authors.initials: MR
authors.lastname: Tracey
mesh_terms: D000577:Amides / Q000138:chemical synthesis*; D001965:Bromides / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D047028:Macrocyclic Compounds / Q000138:chemical synthesis*; D008968:Molecular Conformation
chemical_list: D000577:Amides; D001965:Bromides; D047028:Macrocyclic Compounds; D003300:Copper