Anion‐Dependent Imidazolium‐Based Catalysts for Allylation of Aniline with Tunable Regioselectivity
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http://hdl.handle.net/10045/107380
Títol: | Anion‐Dependent Imidazolium‐Based Catalysts for Allylation of Aniline with Tunable Regioselectivity |
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Autors: | Albert-Soriano, María | Pastor, Isidro M. |
Grups d'investigació o GITE: | Alternative Methodologies In Chemistry (AMIC) | Nuevos Materiales y Catalizadores (MATCAT) |
Centre, Departament o Servei: | Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica |
Paraules clau: | Allylic Substitution | Heterogeneous catalysis | Imidazolium salt | Metal-free | Regioselectivity | Sustainability |
Àrees de coneixement: | Química Orgánica |
Data de publicació: | 15-de juny-2020 |
Editor: | Wiley-VCH Verlag GmbH & Co. KGaA |
Citació bibliogràfica: | Advanced Synthesis & Catalysis. 2020, 362(12): 2494-2502. doi:10.1002/adsc.202000102 |
Resum: | Metal‐free catalysts based on 1,3‐bis(carboxymethyl)imidazolium halides mediate the reaction between allylic alcohols and anilines, providing the corresponding N ‐, 2‐ and 4‐allylaniline isomers selectively. The imidazolium counterion plays a crucial role in the outcome of the reaction. Thus, while the imidazolium chloride selectively provides the N ‐substituted aniline, the bromide and iodide imidazolium salts produce the 2‐ and 4‐allylaniline isomers, respectively, with excellent selectivities. A set of complementary catalysts, which are available by simple modulation, is here presented to conduct a highly regioselective allylation reaction of anilines. Not only the catalysts are synthesized in a straightforward and easily scalable manner, but they can be recycled and used under solvent‐free reaction condition, due to the favorable interactions with the reactants. |
Patrocinadors: | This work was financially supported by the University of Alicante (VIGROB-173, VIGROB-285 and VIGROB-316FI), the Spanish Ministerio de Economía y Competitividad (CTQ2015-66624-P, CTQ2017-88171-P), the Spanish Ministerio de Ciencia, Innovación y Universidades (PGC2018-096616-B-I00) and the Generalitat Valenciana (AICO/2017/007). M.A.-S. thanks the Spanish Ministerio de Educación, Cultura y Deporte for a predoctoral fellowship (FPU15/06040). |
URI: | http://hdl.handle.net/10045/107380 |
ISSN: | 1615-4150 (Print) | 1615-4169 (Online) |
DOI: | 10.1002/adsc.202000102 |
Idioma: | eng |
Tipus: | info:eu-repo/semantics/article |
Drets: | © 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim |
Revisió científica: | si |
Versió de l'editor: | https://doi.org/10.1002/adsc.202000102 |
Apareix a la col·lecció: | INV - AMIC - Artículos de Revistas INV - MATCAT - Artículos de Revistas |
Arxius per aquest ítem:
Arxiu | Descripció | Tamany | Format | |
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Albert-Soriano_Pastor_2020_AdvSynthCatal_final.pdf | Versión final (acceso restringido) | 5,34 MB | Adobe PDF | Obrir Sol·licitar una còpia |
Albert-Soriano_Pastor_2020_AdvSynthCatal_accepted.pdf | Accepted Manuscript (acceso abierto) | 2,31 MB | Adobe PDF | Obrir Vista prèvia |
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