Palladium-Catalysed C2 or C5 Direct Arylation of 3-Substituted Thiophenes with Aryl Bromides
| Autor: | Marina Ionita, Reny Jacob Roy, Henri Doucet, Jia Jia Dong, David Roy |
|---|---|
| Přispěvatelé: | Institut des Sciences Chimiques de Rennes (ISCR), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS) |
| Jazyk: | angličtina |
| Rok vydání: | 2011 |
| Předmět: |
Nitrile
catalysis 010405 organic chemistry Aryl Organic Chemistry Substituent Regioselectivity chemistry.chemical_element [CHIM.CATA]Chemical Sciences/Catalysis 010402 general chemistry palladium 01 natural sciences Medicinal chemistry 0104 chemical sciences Catalysis chemistry.chemical_compound C-H bond activation chemistry Bromide thiophenes Thiophene arylation Palladium |
| Zdroj: | SYNTHESIS SYNTHESIS, Georg Thieme Verlag, 2011, 21, pp.3530-3546. ⟨10.1055/s-0030-1260213⟩ Synthesis: Journal of Synthetic Organic Chemistry Synthesis: Journal of Synthetic Organic Chemistry, 2011, 21, pp.3530-3546. ⟨10.1055/s-0030-1260213⟩ |
| ISSN: | 0039-7881 1437-210X |
| DOI: | 10.1055/s-0030-1260213⟩ |
| Popis: | International audience; The Pd(OAc)2/dppb system was found to be an efficient catalyst for the direct arylation of 3-substituted thiophene derivatives. The regioselectivity of the arylation strongly depends on the thiophene substituent and also on the nature of the aryl bromide. When using 3-formyl, 3-cyano, 3-methyl, 3-hydroxymethyl or 3-bromothiophene, the 2-arylated thiophenes were obtained with 76-95% regioselectivity; whereas, the arylation of 3-formylthiophene diethylacetal or 3-acetylthiophene gave the 5-arylated thiophenes with 52-90% regioselectivity. The use of congested aryl bromides favours the arylation at C5. These reactions were performed using only 0.1 mol% of catalyst. Moreover, this procedure has been found to be tolerant to a variety of functional groups on the aryl bromide such as formyl, propionyl, benzoyl, nitrile, and nitro. |
| Databáze: | OpenAIRE |
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