title: A simple, modular synthesis of substituted pyridines.
abstract: 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.
authors.affiliation: Department of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, Georgia 30322, USA.
authors.forename: Songbai
authors.initials: S
authors.lastname: Liu
authors.forename: Lanny S
authors.initials: LS
authors.lastname: Liebeskind
mesh_terms: D001897:Boronic Acids / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D010091:Oximes / Q000737:chemistry; D011725:Pyridines / Q000138:chemical synthesis*
chemical_list: D001897:Boronic Acids; D010091:Oximes; D011725:Pyridines; D003300:Copper