title: Synthesis of benzo-fused heterocycles by intramolecular α-arylation of ketone enolate anions.
abstract: A two-step synthesis of six-, seven-, eight-, and nine-member benzo-fused heterocycles in good to excellent yields is reported. The synthetic strategy involves the generation of a new intramolecular α-aryl ketone bond by the photostimulated S(RN)1 reaction of ketone enolate anions linked to a pendant haloarene as the key step. On the other hand, an intramolecular C(Ar)-C(Ar) coupling led to the formation of five- and six-member benzo-fused heterocycles (9H-carbazole and phenanthridine) when an aromatic amide anion is competitively formed.
authors.affiliation: INFIQC, Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, X5000HUA Córdoba, Argentina.
authors.forename: Javier F
authors.initials: JF
authors.lastname: Guastavino
authors.forename: Roberto A
authors.initials: RA
authors.lastname: Rossi
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000838:Anions / Q000737:chemistry*; D002227:Carbazoles / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D007659:Ketones / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D010617:Phenanthridines / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000838:Anions; D002227:Carbazoles; D007659:Ketones; D010617:Phenanthridines; C041514:carbazole; D010165:Palladium