Reactivity of bromoselenophenes in palladium-catalyzed direct arylations
The reactivity of 2-bromo- and 2,5-dibromoselenophenes in Pd-catalyzed direct heteroarylation was investigated. From 2-bromoselenophene, only the most reactive heteroarenes could be employed to prepare 2-heteroarylated selenophenes; whereas, 2,5-dibromoselenophene generally gave 2,5-di(heteroarylate...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2017-12-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.13.278 |
| _version_ | 1831525554786926592 |
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| author | Aymen Skhiri Ridha Ben Salem Jean-François Soulé Henri Doucet |
| author_facet | Aymen Skhiri Ridha Ben Salem Jean-François Soulé Henri Doucet |
| author_sort | Aymen Skhiri |
| collection | DOAJ |
| description | The reactivity of 2-bromo- and 2,5-dibromoselenophenes in Pd-catalyzed direct heteroarylation was investigated. From 2-bromoselenophene, only the most reactive heteroarenes could be employed to prepare 2-heteroarylated selenophenes; whereas, 2,5-dibromoselenophene generally gave 2,5-di(heteroarylated) selenophenes in high yields using both thiazole and thiophene derivatives. Moreover, sequential catalytic C2 heteroarylation, bromination, catalytic C5 arylation reactions allowed the synthesis of unsymmetrical 2,5-di(hetero)arylated selenophene derivatives in three steps from selenophene. |
| first_indexed | 2024-12-16T15:53:24Z |
| format | Article |
| id | doaj.art-47b51a78d0b5414bb4953bbcb062c412 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-16T15:53:24Z |
| publishDate | 2017-12-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-47b51a78d0b5414bb4953bbcb062c4122022-12-21T22:25:38ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972017-12-011312862286810.3762/bjoc.13.2781860-5397-13-278Reactivity of bromoselenophenes in palladium-catalyzed direct arylationsAymen Skhiri0Ridha Ben Salem1Jean-François Soulé2Henri Doucet3Institut des Sciences Chimiques de Rennes, UMR 6226 CNRS-Université de Rennes 1, "Organométalliques: Matériaux et Catalyse", Campus de Beaulieu, 35042 Rennes, FranceLaboratoire de Laboratoire de Chimie Organique LR 17ES08, Université de Sfax, Faculté des Sciences de Sfax, Route de la Soukra km 4, 3038 Sfax, TunisiaInstitut des Sciences Chimiques de Rennes, UMR 6226 CNRS-Université de Rennes 1, "Organométalliques: Matériaux et Catalyse", Campus de Beaulieu, 35042 Rennes, FranceInstitut des Sciences Chimiques de Rennes, UMR 6226 CNRS-Université de Rennes 1, "Organométalliques: Matériaux et Catalyse", Campus de Beaulieu, 35042 Rennes, FranceThe reactivity of 2-bromo- and 2,5-dibromoselenophenes in Pd-catalyzed direct heteroarylation was investigated. From 2-bromoselenophene, only the most reactive heteroarenes could be employed to prepare 2-heteroarylated selenophenes; whereas, 2,5-dibromoselenophene generally gave 2,5-di(heteroarylated) selenophenes in high yields using both thiazole and thiophene derivatives. Moreover, sequential catalytic C2 heteroarylation, bromination, catalytic C5 arylation reactions allowed the synthesis of unsymmetrical 2,5-di(hetero)arylated selenophene derivatives in three steps from selenophene.https://doi.org/10.3762/bjoc.13.278C–H bond activationcatalysisheteroarenespalladiumselenophene |
| spellingShingle | Aymen Skhiri Ridha Ben Salem Jean-François Soulé Henri Doucet Reactivity of bromoselenophenes in palladium-catalyzed direct arylations Beilstein Journal of Organic Chemistry C–H bond activation catalysis heteroarenes palladium selenophene |
| title | Reactivity of bromoselenophenes in palladium-catalyzed direct arylations |
| title_full | Reactivity of bromoselenophenes in palladium-catalyzed direct arylations |
| title_fullStr | Reactivity of bromoselenophenes in palladium-catalyzed direct arylations |
| title_full_unstemmed | Reactivity of bromoselenophenes in palladium-catalyzed direct arylations |
| title_short | Reactivity of bromoselenophenes in palladium-catalyzed direct arylations |
| title_sort | reactivity of bromoselenophenes in palladium catalyzed direct arylations |
| topic | C–H bond activation catalysis heteroarenes palladium selenophene |
| url | https://doi.org/10.3762/bjoc.13.278 |
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