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Abstract:

A convenient methodology for the synthesis of 3-sustituted-2,3- dihydrobenzofurans was developed based on the tandem intramolecular carbolithiation-cyclization of 2-bromophenyl-3-phenylprop-2-enyl ether, followed by trapping of the new lithiated intermediate by suitable electrophiles. Several electrophiles were tested, affording good to excellent yields. Alkyl bromides show better results than chlorides and when doubly halogenated alkyl chains are used as electrophiles only one position reacts, affording substituted benzofurans conveniently functionalized to undergo further reactions. The performance of both butyl and phenyllithium as lithiating agents was examined. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource(s): Full experimental and spectral details.] © 2014 Taylor and Francis Group, LLC.

Registro:

Documento: Artículo
Título:Synthesis of substituted benzofurans by the tandem one-pot intramolecular carbolithiation-cyclization-substitution sequence
Autor:Rodríguez, C.; Nudelman, N.S.
Filiación:Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, C1428EGA Buenos Aires, Argentina
Palabras clave:Alkylation; benzofurans; intramolecular carbocyclization; intramolecular carbolithiation; organolithium
Año:2014
Volumen:44
Número:6
Página de inicio:772
Página de fin:778
DOI: http://dx.doi.org/10.1080/00397911.2013.830132
Título revista:Synthetic Communications
Título revista abreviado:Synth. Commun.
ISSN:00397911
CODEN:SYNCA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00397911_v44_n6_p772_Rodriguez

Referencias:

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Citas:

---------- APA ----------
Rodríguez, C. & Nudelman, N.S. (2014) . Synthesis of substituted benzofurans by the tandem one-pot intramolecular carbolithiation-cyclization-substitution sequence. Synthetic Communications, 44(6), 772-778.
http://dx.doi.org/10.1080/00397911.2013.830132
---------- CHICAGO ----------
Rodríguez, C., Nudelman, N.S. "Synthesis of substituted benzofurans by the tandem one-pot intramolecular carbolithiation-cyclization-substitution sequence" . Synthetic Communications 44, no. 6 (2014) : 772-778.
http://dx.doi.org/10.1080/00397911.2013.830132
---------- MLA ----------
Rodríguez, C., Nudelman, N.S. "Synthesis of substituted benzofurans by the tandem one-pot intramolecular carbolithiation-cyclization-substitution sequence" . Synthetic Communications, vol. 44, no. 6, 2014, pp. 772-778.
http://dx.doi.org/10.1080/00397911.2013.830132
---------- VANCOUVER ----------
Rodríguez, C., Nudelman, N.S. Synthesis of substituted benzofurans by the tandem one-pot intramolecular carbolithiation-cyclization-substitution sequence. Synth. Commun. 2014;44(6):772-778.
http://dx.doi.org/10.1080/00397911.2013.830132