1,3-Bis(carboxymethyl)imidazolium Chloride as a Metal-Free and Recyclable Catalyst for the Synthesis of N-Allylanilines by Allylic Substitution of Alcohols
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Título: | 1,3-Bis(carboxymethyl)imidazolium Chloride as a Metal-Free and Recyclable Catalyst for the Synthesis of N-Allylanilines by Allylic Substitution of Alcohols |
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Autor/es: | Albert-Soriano, María | Hernández-Martínez, Laura | Pastor, Isidro M. |
Grupo/s de investigación o GITE: | Nuevos Materiales y Catalizadores (MATCAT) |
Centro, Departamento o Servicio: | Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica |
Palabras clave: | Allylic anilines | Allylic substitution | Imidazolium salt | Metal-free | Sustainable |
Área/s de conocimiento: | Química Orgánica |
Fecha de publicación: | 21-sep-2018 |
Editor: | American Chemical Society |
Cita bibliográfica: | ACS Sustainable Chemistry and Engineering. 2018, 6(11): 14063-14070. doi:10.1021/acssuschemeng.8b02614 |
Resumen: | The 1,3-bis(carboxymethyl)imidazolium chloride, which is easily and in a straightforward manner prepared readily from starting materials in multigram scale, is employed as catalyst in the synthesis of N-allylanilines by allylic substitution of alcohols with anilines. This metal-free catalyst allows the reaction to be carried out under mild reaction conditions (80 °C and air open vessel) and proved to be efficient for a diversity of anilines and allylic alcohols, providing exclusively the product of N-substitution independently of the substituents in the aniline reactant. The process described is simple and effective, allowing N-allylanilines to be obtained in preparative scale [e.g., 3.30 g of N-(1,3-diphenylallyl)-4-nitroaniline]. The catalyst could be reused up to 15 cycles without loss of activity, proving its robustness. |
Patrocinador/es: | This work was financially supported by the University of Alicante (VIGROB-285) and the Spanish Ministerio de Economía y Competitividad (CTQ2015-66624-P). M.A.S. thanks the Spanish Ministerio de Educación, Cultura y Deporte for a predoctoral fellowship (FPU15/06040). |
URI: | http://hdl.handle.net/10045/82848 |
ISSN: | 2168-0485 |
DOI: | 10.1021/acssuschemeng.8b02614 |
Idioma: | eng |
Tipo: | info:eu-repo/semantics/article |
Derechos: | © 2018 American Chemical Society |
Revisión científica: | si |
Versión del editor: | https://doi.org/10.1021/acssuschemeng.8b02614 |
Aparece en las colecciones: | INV - AMIC - Artículos de Revistas INV - MATCAT - Artículos de Revistas |
Archivos en este ítem:
Archivo | Descripción | Tamaño | Formato | |
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2018_Albert-Soriano_etal_ACSSustainableChemEng_accepted.pdf | Accepted Manuscript (acceso abierto) | 531,59 kB | Adobe PDF | Abrir Vista previa |
2018_Albert-Soriano_etal_ACSSustainableChemEng_final.pdf | Versión final (acceso restringido) | 2,53 MB | Adobe PDF | Abrir Solicitar una copia |
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