title: Synthesis of benzo- and naphtho-fused bicyclo[n.3.1]alkane frameworks with a bridgehead nitrogen function by palladium-catalyzed intramolecular α'-arylation of α-nitroketones.
abstract: The C-alkylation of cyclic α-nitroketones with α-halobenzyl halides in the presence of DBU followed by a Pd-catalyzed intramolecular C-arylation afforded benzo-and naphtho-fused bicyclo[n.3.1]alkane derivatives (n = 3, 4, 5) in excellent overall yields for the two-step sequence. In some of the reactions starting from α-nitrocyclooctanone, the major products were fused indane derivatives arising from an intramolecular attack of an intermediate Pd species onto the carbonyl group, followed by elimination.
authors.affiliation: Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense, 28040 Madrid, Spain.
authors.forename: Giorgio
authors.initials: G
authors.lastname: Giorgi
authors.forename: Swarupananda
authors.initials: S
authors.lastname: Maiti
authors.forename: Pilar
authors.initials: P
authors.lastname: López-Alvarado
authors.forename: J Carlos
authors.initials: JC
authors.lastname: Menéndez
mesh_terms: D000473:Alkanes / Q000138:chemical synthesis*; D001554:Benzene / Q000737:chemistry; D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D002384:Catalysis; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D009284:Naphthols / Q000737:chemistry; D009574:Nitro Compounds / Q000737:chemistry*; D009584:Nitrogen / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*
chemical_list: D000473:Alkanes; D001643:Bridged Bicyclo Compounds; D007659:Ketones; D009284:Naphthols; D009574:Nitro Compounds; D010165:Palladium; D001554:Benzene; D009584:Nitrogen