Cargando…

Regiocontroled Pd-catalysed C5-arylation of 3-substituted thiophene derivatives using a bromo-substituent as blocking group

The use of a bromo-substituent as blocking group at the C2-position of 3-substituted thiophenes allows the regioselective introduction of aryl substituents at C5-position via Pd-catalysed direct arylation. With 1 mol % of a phosphine-free Pd catalyst, KOAc as the base and DMA as the solvent and vari...

Descripción completa

Detalles Bibliográficos
Autores principales: Brahim, Mariem, Ben Ammar, Hamed, Soulé, Jean-François, Doucet, Henri
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5082451/
https://www.ncbi.nlm.nih.gov/pubmed/27829927
http://dx.doi.org/10.3762/bjoc.12.210
_version_ 1782463057819074560
author Brahim, Mariem
Ben Ammar, Hamed
Soulé, Jean-François
Doucet, Henri
author_facet Brahim, Mariem
Ben Ammar, Hamed
Soulé, Jean-François
Doucet, Henri
author_sort Brahim, Mariem
collection PubMed
description The use of a bromo-substituent as blocking group at the C2-position of 3-substituted thiophenes allows the regioselective introduction of aryl substituents at C5-position via Pd-catalysed direct arylation. With 1 mol % of a phosphine-free Pd catalyst, KOAc as the base and DMA as the solvent and various electron-deficient aryl bromides as aryl sources, C5-(hetero)arylated thiophenes were synthesized in moderate to high yields, without cleavage of the thienyl C–Br bond. Moreover, sequential direct thienyl C5-arylation followed by Pd-catalysed direct arylation or Suzuki coupling at the C2-position allows to prepare 2,5-di(hetero)arylated thiophenes bearing two different (hetero)aryl units in only two steps. This method provides a “green” access to arylated thiophene derivatives as it reduces the number of steps to prepare these compounds and also the formation of wastes.
format Online
Article
Text
id pubmed-5082451
institution National Center for Biotechnology Information
language English
publishDate 2016
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-50824512016-11-09 Regiocontroled Pd-catalysed C5-arylation of 3-substituted thiophene derivatives using a bromo-substituent as blocking group Brahim, Mariem Ben Ammar, Hamed Soulé, Jean-François Doucet, Henri Beilstein J Org Chem Full Research Paper The use of a bromo-substituent as blocking group at the C2-position of 3-substituted thiophenes allows the regioselective introduction of aryl substituents at C5-position via Pd-catalysed direct arylation. With 1 mol % of a phosphine-free Pd catalyst, KOAc as the base and DMA as the solvent and various electron-deficient aryl bromides as aryl sources, C5-(hetero)arylated thiophenes were synthesized in moderate to high yields, without cleavage of the thienyl C–Br bond. Moreover, sequential direct thienyl C5-arylation followed by Pd-catalysed direct arylation or Suzuki coupling at the C2-position allows to prepare 2,5-di(hetero)arylated thiophenes bearing two different (hetero)aryl units in only two steps. This method provides a “green” access to arylated thiophene derivatives as it reduces the number of steps to prepare these compounds and also the formation of wastes. Beilstein-Institut 2016-10-17 /pmc/articles/PMC5082451/ /pubmed/27829927 http://dx.doi.org/10.3762/bjoc.12.210 Text en Copyright © 2016, Brahim et al. https://creativecommons.org/licenses/by/4.0https://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/4.0), 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
Brahim, Mariem
Ben Ammar, Hamed
Soulé, Jean-François
Doucet, Henri
Regiocontroled Pd-catalysed C5-arylation of 3-substituted thiophene derivatives using a bromo-substituent as blocking group
title Regiocontroled Pd-catalysed C5-arylation of 3-substituted thiophene derivatives using a bromo-substituent as blocking group
title_full Regiocontroled Pd-catalysed C5-arylation of 3-substituted thiophene derivatives using a bromo-substituent as blocking group
title_fullStr Regiocontroled Pd-catalysed C5-arylation of 3-substituted thiophene derivatives using a bromo-substituent as blocking group
title_full_unstemmed Regiocontroled Pd-catalysed C5-arylation of 3-substituted thiophene derivatives using a bromo-substituent as blocking group
title_short Regiocontroled Pd-catalysed C5-arylation of 3-substituted thiophene derivatives using a bromo-substituent as blocking group
title_sort regiocontroled pd-catalysed c5-arylation of 3-substituted thiophene derivatives using a bromo-substituent as blocking group
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5082451/
https://www.ncbi.nlm.nih.gov/pubmed/27829927
http://dx.doi.org/10.3762/bjoc.12.210
work_keys_str_mv AT brahimmariem regiocontroledpdcatalysedc5arylationof3substitutedthiophenederivativesusingabromosubstituentasblockinggroup
AT benammarhamed regiocontroledpdcatalysedc5arylationof3substitutedthiophenederivativesusingabromosubstituentasblockinggroup
AT soulejeanfrancois regiocontroledpdcatalysedc5arylationof3substitutedthiophenederivativesusingabromosubstituentasblockinggroup
AT doucethenri regiocontroledpdcatalysedc5arylationof3substitutedthiophenederivativesusingabromosubstituentasblockinggroup