1,2-Functionalized Imidazoles as Palladium Ligands: An Efficient and Robust Catalytic System for the Fluorine-Free Hiyama Reaction
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Título: | 1,2-Functionalized Imidazoles as Palladium Ligands: An Efficient and Robust Catalytic System for the Fluorine-Free Hiyama Reaction |
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Autor/es: | Martínez Flores, Regina | Pastor, Isidro M. | Yus, Miguel |
Grupo/s de investigación o GITE: | Nuevos Materiales y Catalizadores (MATCAT) | Síntesis Asimétrica (SINTAS) |
Centro, Departamento o Servicio: | Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica |
Palabras clave: | Synthetic methods | Nitrogen heterocycles | Palladium | Ligand design | Cross-coupling |
Área/s de conocimiento: | Química Orgánica |
Fecha de publicación: | feb-2014 |
Editor: | Wiley-VCH Verlag GmbH & Co. KGaA |
Cita bibliográfica: | European Journal of Organic Chemistry. 2014, 4: 872-877. doi:10.1002/ejoc.201301439 |
Resumen: | A variety of hydroxy- and amino-functionalized imidazoles were prepared from 1-methyl- and 1-(diethoxymethyl)imidazole by means of isoprene-mediated lithiation followed by reaction with an electrophile. These compounds in combination with palladium acetate were screened as catalyst systems for the Hiyama reaction under fluorine-free conditions using microwave irradiation. The systematic study of the catalytic system showed 1-methyl-2-aminoalkylimidazole derivative L1 to be the best ligand, which was employed under solvent-free conditions with a 1:2 Pd/ligand ratio and TBAB (20 mol-%) as additive. The study has revealed an interaction between the Pd/ligand ratio and the amount of TBAB. The established catalytic system presented a certain degree of robustness, and it has been successfully employed in the coupling of a range of aryl bromides and chlorides with different aryl siloxanes. Furthermore, both reagents were employed in an equimolecular amount, without an excess of organosilane. |
Patrocinador/es: | Financial support from the Spanish Ministerio de Ciencia e Innovación (MICINN) (project numbers CTQ2007-65218, CTQ2011-24165), from Consolider Ingenio 2010 (CSD2007-00006), from the Generalitat Valenciana (PROMETEO/2009/039), from the Fondos Europeos para el Desarrollo Regional (FEDER) and from the Universidad de Alicante is acknowledged. |
URI: | http://hdl.handle.net/10045/46299 |
ISSN: | 1434-193X (Print) | 1099-0690 (Online) |
DOI: | 10.1002/ejoc.201301439 |
Idioma: | eng |
Tipo: | info:eu-repo/semantics/article |
Derechos: | © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim |
Revisión científica: | si |
Versión del editor: | http://dx.doi.org/10.1002/ejoc.201301439 |
Aparece en las colecciones: | INV - SINTAS - Artículos de Revistas INV - MATCAT - Artículos de Revistas INV - AMIC - Artículos de Revistas |
Archivos en este ítem:
Archivo | Descripción | Tamaño | Formato | |
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2014_Martinez_etal_EurJOC_final.pdf | Versión final (acceso restringido) | 646,73 kB | Adobe PDF | Abrir Solicitar una copia |
2014_Martinez_etal_EurJOC_preprint.pdf | Preprint (acceso abierto) | 352,31 kB | Adobe PDF | Abrir Vista previa |
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