A simple, modular synthesis of substituted pyridines.
A simple, modular method to prepare highly substituted pyridines is disclosed. The method employs a cascade reaction comprising (1) a novel N-iminative, Cu-catalyzed cross-coupling of alkenylboronic acids at the N-O bond of alpha,beta-unsaturated ketoxime O-pentafluorobenzoates, (2) electrocyclization of the resulting 3-azatriene, and (3) air oxidation affording highly substituted pyridines in moderate to excellent isolated yields (43-91%). Starting materials are readily available, and functional group tolerance is very good.
Liu
Songbai
S
Department of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, Georgia 30322, USA.
Liebeskind
Lanny S
LS
D001897:Boronic Acids / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D010091:Oximes / Q000737:chemistry; D011725:Pyridines / Q000138:chemical synthesis*
D001897:Boronic Acids; D010091:Oximes; D011725:Pyridines; D003300:Copper