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Abstract:

The aim of this review is to illustrate what we have dubbed an aromatic carbon-carbon ipso-substitution reaction in which a new Ar-C bond is formed at the expense of another Ar-C bond. The potentiality of several C-based leaving groups including alkyl, carbinol, CN, COOH, and carbonyl groups in arylation reactions will be illustrated accordingly for the preparation of biphenyl-, vinyl-, alkynyl-, and alkyl-substituted aromatics. Getting the bond back together: The strategies are unveiled for an aromatic C-C ipso-substitution reaction. This process allows for the one-pot cleavage of Ar-C bonds (e.g., in alkyl and acyl (hetero)aromatics, in benzonitriles, in α,α- disubstituted arylmethanols, and in carboxylic acids) for the formation of a new Ar-C bond (see picture). Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Registro:

Documento: Artículo
Título:The aromatic carbon-carbon ipso-substitution reaction
Autor:Bonesi, S.M.; Fagnoni, M.
Filiación:Department of Organic Chemistry, University of Pavia, Via Taramelli 10, Italy
CIHIDECAR-CONICET, Departamento de Química Orgánica, Ciudad Universitaria, 3er Piso, Pabellón 2, Argentina
Palabras clave:Ar-C bonds; aromatic substitution; arylation; C-based leaving groups; cleavage reactions; Ar-C bonds; Aromatic substitutions; Arylations; Cleavage reaction; Leaving groups; Alkylation; Argon; Aromatization; Carboxylic acids; Methanol; Substitution reactions; Aromatic compounds
Año:2010
Volumen:16
Número:46
Página de inicio:13572
Página de fin:13589
DOI: http://dx.doi.org/10.1002/chem.201001478
Título revista:Chemistry - A European Journal
Título revista abreviado:Chem. Eur. J.
ISSN:09476539
CODEN:CEUJE
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09476539_v16_n46_p13572_Bonesi

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Citas:

---------- APA ----------
Bonesi, S.M. & Fagnoni, M. (2010) . The aromatic carbon-carbon ipso-substitution reaction. Chemistry - A European Journal, 16(46), 13572-13589.
http://dx.doi.org/10.1002/chem.201001478
---------- CHICAGO ----------
Bonesi, S.M., Fagnoni, M. "The aromatic carbon-carbon ipso-substitution reaction" . Chemistry - A European Journal 16, no. 46 (2010) : 13572-13589.
http://dx.doi.org/10.1002/chem.201001478
---------- MLA ----------
Bonesi, S.M., Fagnoni, M. "The aromatic carbon-carbon ipso-substitution reaction" . Chemistry - A European Journal, vol. 16, no. 46, 2010, pp. 13572-13589.
http://dx.doi.org/10.1002/chem.201001478
---------- VANCOUVER ----------
Bonesi, S.M., Fagnoni, M. The aromatic carbon-carbon ipso-substitution reaction. Chem. Eur. J. 2010;16(46):13572-13589.
http://dx.doi.org/10.1002/chem.201001478