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INFIQC, Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciudad Universitaria, Córdoba, 5000, Argentina
E-mail: rossi@fcq.unc.edu.ar
; Fax: +54 351 4333030
Org. Biomol. Chem., 2012,10, 9255-9261
DOI:
10.1039/C2OB26698A
Received
28 Aug 2012,
Accepted
02 Oct 2012
First published online
02 Oct 2012
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.
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Organic & Biomolecular Chemistry
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