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.
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.
Zhang
Xuejun
X
Division of Pharmaceutical Sciences, 777 Highland Avenue, University of Wisconsin, Madison, Wisconsin 53705, USA.
Zhang
Yanshi
Y
Huang
Jian
J
Hsung
Richard P
RP
Kurtz
Kimberly C M
KC
Oppenheimer
Jossian
J
Petersen
Matthew E
ME
Sagamanova
Irina K
IK
Shen
Lichun
L
Tracey
Michael R
MR
D000577:Amides / Q000138:chemical synthesis*; D001965:Bromides / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D047028:Macrocyclic Compounds / Q000138:chemical synthesis*; D008968:Molecular Conformation
D000577:Amides; D001965:Bromides; D047028:Macrocyclic Compounds; D003300:Copper