Copper-promoted hydration and annulation of 2-fluorophenylacetylene derivatives: from alkynes to benzo[b]furans and benzo[b]thiophenes

An efficient copper-promoted hydration reaction and its application in the synthesis of benzo[b]furan and benzo[b]thiophene derivatives is presented starting from readily available 2-fluorophenylacetylene derivatives. The key annulation step involves the hydration of the C–F bond of 2-fluorophenylac...

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Detalles Bibliográficos
Autores principales: Li, Yibiao, Cheng, Liang, Liu, Xiaohang, Li, Bin, Sun, Ning
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2014
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4273265/
https://www.ncbi.nlm.nih.gov/pubmed/25550754
http://dx.doi.org/10.3762/bjoc.10.305
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author Li, Yibiao
Cheng, Liang
Liu, Xiaohang
Li, Bin
Sun, Ning
author_facet Li, Yibiao
Cheng, Liang
Liu, Xiaohang
Li, Bin
Sun, Ning
author_sort Li, Yibiao
collection PubMed
description An efficient copper-promoted hydration reaction and its application in the synthesis of benzo[b]furan and benzo[b]thiophene derivatives is presented starting from readily available 2-fluorophenylacetylene derivatives. The key annulation step involves the hydration of the C–F bond of 2-fluorophenylacetylene derivatives followed by an intramolecular annulation to afford benzo[b]furan and benzo[b]thiophene derivatives. Moreover, structurally important 2,2'-bisbenzofuran scaffolds are provided in good yields.
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spelling pubmed-42732652014-12-30 Copper-promoted hydration and annulation of 2-fluorophenylacetylene derivatives: from alkynes to benzo[b]furans and benzo[b]thiophenes Li, Yibiao Cheng, Liang Liu, Xiaohang Li, Bin Sun, Ning Beilstein J Org Chem Full Research Paper An efficient copper-promoted hydration reaction and its application in the synthesis of benzo[b]furan and benzo[b]thiophene derivatives is presented starting from readily available 2-fluorophenylacetylene derivatives. The key annulation step involves the hydration of the C–F bond of 2-fluorophenylacetylene derivatives followed by an intramolecular annulation to afford benzo[b]furan and benzo[b]thiophene derivatives. Moreover, structurally important 2,2'-bisbenzofuran scaffolds are provided in good yields. Beilstein-Institut 2014-12-04 /pmc/articles/PMC4273265/ /pubmed/25550754 http://dx.doi.org/10.3762/bjoc.10.305 Text en Copyright © 2014, Li 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
Li, Yibiao
Cheng, Liang
Liu, Xiaohang
Li, Bin
Sun, Ning
Copper-promoted hydration and annulation of 2-fluorophenylacetylene derivatives: from alkynes to benzo[b]furans and benzo[b]thiophenes
title Copper-promoted hydration and annulation of 2-fluorophenylacetylene derivatives: from alkynes to benzo[b]furans and benzo[b]thiophenes
title_full Copper-promoted hydration and annulation of 2-fluorophenylacetylene derivatives: from alkynes to benzo[b]furans and benzo[b]thiophenes
title_fullStr Copper-promoted hydration and annulation of 2-fluorophenylacetylene derivatives: from alkynes to benzo[b]furans and benzo[b]thiophenes
title_full_unstemmed Copper-promoted hydration and annulation of 2-fluorophenylacetylene derivatives: from alkynes to benzo[b]furans and benzo[b]thiophenes
title_short Copper-promoted hydration and annulation of 2-fluorophenylacetylene derivatives: from alkynes to benzo[b]furans and benzo[b]thiophenes
title_sort copper-promoted hydration and annulation of 2-fluorophenylacetylene derivatives: from alkynes to benzo[b]furans and benzo[b]thiophenes
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4273265/
https://www.ncbi.nlm.nih.gov/pubmed/25550754
http://dx.doi.org/10.3762/bjoc.10.305
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