Functionalization of the 3-Position of Thiophene and Benzo[b]-thiophene Moieties by Palladium-Catalyzed CC Bond Forming Reactions using Diazonium Salts
he palladium-catalyzed Matsuda-Heck and Suzuki-Miyaura cross-couplings of 2-methoxycarbonylthiophene-3-diazonium tetrafluoroborate 1 were performed to synthesize a series of thiophene derivatives functionalized in the β-position. Good to excellent yields of the cross-coupling products were obtained...
| Autores: | , , , , |
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| Tipo de recurso: | artículo |
| Estado: | Versión publicada |
| Fecha de publicación: | 2011 |
| País: | España |
| Institución: | Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya) |
| Repositorio: | Recercat. Dipósit de la Recerca de Catalunya |
| OAI Identifier: | oai:recercat.cat:10256/15491 |
| Acceso en línea: | http://hdl.handle.net/10256/15491 |
| Access Level: | acceso embargado |
| Palabra clave: | Suzuki-Miyaura cross-couplings Reaccions químiques Chemical reactions Matsuda-Heck, Reacció de Matsuda-Heck reaction Catalitzadors de pal·ladi Palladium catalysts Alquens Alkenes |
| Sumario: | he palladium-catalyzed Matsuda-Heck and Suzuki-Miyaura cross-couplings of 2-methoxycarbonylthiophene-3-diazonium tetrafluoroborate 1 were performed to synthesize a series of thiophene derivatives functionalized in the β-position. Good to excellent yields of the cross-coupling products were obtained using palladium acetate [Pd(OAc) 2 ], a ligandless palladium catalyst, without a base, at room temperature, under aerobic conditions and with short reaction times. A diazotization and cross-coupling sequence can also be performed in a one-pot process avoiding the isolation of the thiophenediazonium salt derivative. In addition, 2-methoxycarbonylbenzo[b] thiophene-3-diazonium tetrafluoroborate 8 was also efficiently arylated by applying the same Suzuki-Miyaura optimized reaction conditions |
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