An expedient route to heterocycles througha-arylation of ketones and arylamides bymicrowave induced thermal SRN1 reactions
Microwave irradiation promotes a quick aromatic nucleophilic substitution by a thermally induced electrontransfer process to form new C–C bonds by the coupling of aryl radicals and enolate nucleophiles. Diverse2-aryl-1-phenylethanones can be prepared by the directa-arylation of acetophenone with dif...
| Autores: | , , |
|---|---|
| Tipo de recurso: | artículo |
| Estado: | Versión publicada |
| Fecha de publicación: | 2014 |
| País: | Argentina |
| Institución: | Consejo Nacional de Investigaciones Científicas y Técnicas |
| Repositorio: | CONICET Digital (CONICET) |
| Idioma: | inglés |
| OAI Identifier: | oai:ri.conicet.gov.ar:11336/31481 |
| Acceso en línea: | http://hdl.handle.net/11336/31481 |
| Access Level: | acceso abierto |
| Palabra clave: | microwave radical nucleophilic substitution electron transfer ketons https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
| Sumario: | Microwave irradiation promotes a quick aromatic nucleophilic substitution by a thermally induced electrontransfer process to form new C–C bonds by the coupling of aryl radicals and enolate nucleophiles. Diverse2-aryl-1-phenylethanones can be prepared by the directa-arylation of acetophenone with differenthaloarenes. The ketone enolate anion is generated by deprotonation withtBuOK in DMSO and thereaction is carried out in a closed microwave vessel at 70–100 C for 10 min. This simple procedure alsoallows the synthesis of deoxybenzoin and indole heterocycle derivatives by inter- or intra-molecular ringclosure reactions, with moderate to excellent substitution yields. |
|---|