title: Heteroarylation of azine N-oxides.
abstract: Azine N-oxides undergo highly regioselective metalation with TMPZnCl·LiCl under mild conditions. A palladium-catalyzed Negishi cross-coupling reaction of the resulting organozinc species with heteroaromatic bromides provides heterobiaryls specifically oxidized at one nitrogen position in up to 95% yield.
authors.affiliation: Small Molecule Process Chemistry and Discovery Chemistry, Genentech Inc., 1 DNA Way, South San Francisco, California 94080, USA. gosselin.francis@gene.com
authors.forename: Francis
authors.initials: F
authors.lastname: Gosselin
authors.forename: Scott J
authors.initials: SJ
authors.lastname: Savage
authors.forename: Nicole
authors.initials: N
authors.lastname: Blaquiere
authors.forename: Steven T
authors.initials: ST
authors.lastname: Staben
mesh_terms: D001965:Bromides / Q000737:chemistry; D002384:Catalysis; D006571:Heterocyclic Compounds / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010087:Oxides / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001965:Bromides; D006571:Heterocyclic Compounds; D010087:Oxides; D010165:Palladium