Combined directed ortho-zincation and palladium-catalyzed strategies: Synthesis of 4,n-dimethoxy-substituted benzo[b]furans

A new route to regioselectively dialkoxy-functionalized benzo[b]furan derivatives has been developed from 3-halo-2-iodoanisoles bearing an additional methoxy group, which have been accessed through an ortho-zincation/iodination reaction. Two palladium-catalyzed processes, namely a Sonogashira coupli...

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Detalles Bibliográficos
Autores principales: Guilarte, Verónica, Castroviejo, M Pilar, Álvarez, Estela, Sanz, Roberto
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2011
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3182435/
https://www.ncbi.nlm.nih.gov/pubmed/21977210
http://dx.doi.org/10.3762/bjoc.7.146
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author Guilarte, Verónica
Castroviejo, M Pilar
Álvarez, Estela
Sanz, Roberto
author_facet Guilarte, Verónica
Castroviejo, M Pilar
Álvarez, Estela
Sanz, Roberto
author_sort Guilarte, Verónica
collection PubMed
description A new route to regioselectively dialkoxy-functionalized benzo[b]furan derivatives has been developed from 3-halo-2-iodoanisoles bearing an additional methoxy group, which have been accessed through an ortho-zincation/iodination reaction. Two palladium-catalyzed processes, namely a Sonogashira coupling followed by a tandem hydroxylation/cyclization sequence, give rise to new and interesting dimethoxy-substituted benzo[b]furans.
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spelling pubmed-31824352011-10-05 Combined directed ortho-zincation and palladium-catalyzed strategies: Synthesis of 4,n-dimethoxy-substituted benzo[b]furans Guilarte, Verónica Castroviejo, M Pilar Álvarez, Estela Sanz, Roberto Beilstein J Org Chem Full Research Paper A new route to regioselectively dialkoxy-functionalized benzo[b]furan derivatives has been developed from 3-halo-2-iodoanisoles bearing an additional methoxy group, which have been accessed through an ortho-zincation/iodination reaction. Two palladium-catalyzed processes, namely a Sonogashira coupling followed by a tandem hydroxylation/cyclization sequence, give rise to new and interesting dimethoxy-substituted benzo[b]furans. Beilstein-Institut 2011-09-12 /pmc/articles/PMC3182435/ /pubmed/21977210 http://dx.doi.org/10.3762/bjoc.7.146 Text en Copyright © 2011, Guilarte et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Guilarte, Verónica
Castroviejo, M Pilar
Álvarez, Estela
Sanz, Roberto
Combined directed ortho-zincation and palladium-catalyzed strategies: Synthesis of 4,n-dimethoxy-substituted benzo[b]furans
title Combined directed ortho-zincation and palladium-catalyzed strategies: Synthesis of 4,n-dimethoxy-substituted benzo[b]furans
title_full Combined directed ortho-zincation and palladium-catalyzed strategies: Synthesis of 4,n-dimethoxy-substituted benzo[b]furans
title_fullStr Combined directed ortho-zincation and palladium-catalyzed strategies: Synthesis of 4,n-dimethoxy-substituted benzo[b]furans
title_full_unstemmed Combined directed ortho-zincation and palladium-catalyzed strategies: Synthesis of 4,n-dimethoxy-substituted benzo[b]furans
title_short Combined directed ortho-zincation and palladium-catalyzed strategies: Synthesis of 4,n-dimethoxy-substituted benzo[b]furans
title_sort combined directed ortho-zincation and palladium-catalyzed strategies: synthesis of 4,n-dimethoxy-substituted benzo[b]furans
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3182435/
https://www.ncbi.nlm.nih.gov/pubmed/21977210
http://dx.doi.org/10.3762/bjoc.7.146
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