title: Photochemical and photophysical behavior of indolyl anions in photostimulated intramolecular arylation reactions.
abstract: O-Arylation reaction is obtained when N-(2-halophenyl) indolo carboxamides are irradiated in a basic medium. On the basis of photochemical and photophysical experiments, we propose that 2-indolylbenzoxazole is formed by intramolecular electron transfer followed by fast dehalogenation of the halophenyl radical anion pendant moiety, finally a radical-radical collapse renders the observed product.
authors.affiliation: INFIQC, Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciudad Universitaria, Córdoba, 5000, Argentina.
authors.forename: Victoria A
authors.initials: VA
authors.lastname: Vaillard
authors.forename: Roberto A
authors.initials: RA
authors.lastname: Rossi
authors.forename: Juan E
authors.initials: JE
authors.lastname: Argüello
mesh_terms: D000577:Amides / Q000737:chemistry*; D000838:Anions; D001583:Benzoxazoles / Q000138:chemical synthesis*; D004579:Electron Transport; D004583:Electrons; D005609:Free Radicals / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D007700:Kinetics; D008027:Light; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D055668:Photochemical Processes; D013050:Spectrometry, Fluorescence; D013816:Thermodynamics
chemical_list: D000577:Amides; D000838:Anions; D001583:Benzoxazoles; D005609:Free Radicals; D007211:Indoles