Cargando…
Hindered aryl bromides for regioselective palladium-catalysed direct arylation at less favourable C5-carbon of 3-substituted thiophenes
The use of the congested aryl bromide 2-bromo-1,3-dichlorobenzene as coupling partner allows to modify the regioselectivity of the arylation of 3-substituted thiophene derivatives in favour of carbon C5. The coupling of this aryl bromide with a variety of 3-substituted thiophenes gave in all cases t...
Autores principales: | , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Beilstein-Institut
2014
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077437/ https://www.ncbi.nlm.nih.gov/pubmed/24991274 http://dx.doi.org/10.3762/bjoc.10.123 |
_version_ | 1782323602223267840 |
---|---|
author | Jin, Rongwei Bheeter, Charles Beromeo Doucet, Henri |
author_facet | Jin, Rongwei Bheeter, Charles Beromeo Doucet, Henri |
author_sort | Jin, Rongwei |
collection | PubMed |
description | The use of the congested aryl bromide 2-bromo-1,3-dichlorobenzene as coupling partner allows to modify the regioselectivity of the arylation of 3-substituted thiophene derivatives in favour of carbon C5. The coupling of this aryl bromide with a variety of 3-substituted thiophenes gave in all cases the desired 5-arylation products in moderate to good yields using only 0.5 mol % of a phosphine-free and air-stable palladium catalyst. Then, from these 5-arylthiophenes, a second palladium-catalysed C–H bond functionalization at C2 of the thiophene ring allows the synthesis of 2,5-diarylthiophenes with two different aryl units. |
format | Online Article Text |
id | pubmed-4077437 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
spelling | pubmed-40774372014-07-02 Hindered aryl bromides for regioselective palladium-catalysed direct arylation at less favourable C5-carbon of 3-substituted thiophenes Jin, Rongwei Bheeter, Charles Beromeo Doucet, Henri Beilstein J Org Chem Letter The use of the congested aryl bromide 2-bromo-1,3-dichlorobenzene as coupling partner allows to modify the regioselectivity of the arylation of 3-substituted thiophene derivatives in favour of carbon C5. The coupling of this aryl bromide with a variety of 3-substituted thiophenes gave in all cases the desired 5-arylation products in moderate to good yields using only 0.5 mol % of a phosphine-free and air-stable palladium catalyst. Then, from these 5-arylthiophenes, a second palladium-catalysed C–H bond functionalization at C2 of the thiophene ring allows the synthesis of 2,5-diarylthiophenes with two different aryl units. Beilstein-Institut 2014-05-27 /pmc/articles/PMC4077437/ /pubmed/24991274 http://dx.doi.org/10.3762/bjoc.10.123 Text en Copyright © 2014, Jin 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 | Letter Jin, Rongwei Bheeter, Charles Beromeo Doucet, Henri Hindered aryl bromides for regioselective palladium-catalysed direct arylation at less favourable C5-carbon of 3-substituted thiophenes |
title | Hindered aryl bromides for regioselective palladium-catalysed direct arylation at less favourable C5-carbon of 3-substituted thiophenes |
title_full | Hindered aryl bromides for regioselective palladium-catalysed direct arylation at less favourable C5-carbon of 3-substituted thiophenes |
title_fullStr | Hindered aryl bromides for regioselective palladium-catalysed direct arylation at less favourable C5-carbon of 3-substituted thiophenes |
title_full_unstemmed | Hindered aryl bromides for regioselective palladium-catalysed direct arylation at less favourable C5-carbon of 3-substituted thiophenes |
title_short | Hindered aryl bromides for regioselective palladium-catalysed direct arylation at less favourable C5-carbon of 3-substituted thiophenes |
title_sort | hindered aryl bromides for regioselective palladium-catalysed direct arylation at less favourable c5-carbon of 3-substituted thiophenes |
topic | Letter |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077437/ https://www.ncbi.nlm.nih.gov/pubmed/24991274 http://dx.doi.org/10.3762/bjoc.10.123 |
work_keys_str_mv | AT jinrongwei hinderedarylbromidesforregioselectivepalladiumcatalyseddirectarylationatlessfavourablec5carbonof3substitutedthiophenes AT bheetercharlesberomeo hinderedarylbromidesforregioselectivepalladiumcatalyseddirectarylationatlessfavourablec5carbonof3substitutedthiophenes AT doucethenri hinderedarylbromidesforregioselectivepalladiumcatalyseddirectarylationatlessfavourablec5carbonof3substitutedthiophenes |