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...
Autores principales: | , , , |
---|---|
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 |