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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Title: 1,3-Bis(carboxymethyl)imidazolium Chloride as a Metal-Free and Recyclable Catalyst for the Synthesis of N-Allylanilines by Allylic Substitution of Alcohols
Authors: Albert-Soriano, María | Hernández-Martínez, Laura | Pastor, Isidro M.
Research Group/s: Nuevos Materiales y Catalizadores (MATCAT)
Center, Department or Service: Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica
Keywords: Allylic anilines | Allylic substitution | Imidazolium salt | Metal-free | Sustainable
Knowledge Area: Química Orgánica
Issue Date: 21-Sep-2018
Publisher: American Chemical Society
Citation: ACS Sustainable Chemistry and Engineering. 2018, 6(11): 14063-14070. doi:10.1021/acssuschemeng.8b02614
Abstract: 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.
Sponsor: 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
Language: eng
Type: info:eu-repo/semantics/article
Rights: © 2018 American Chemical Society
Peer Review: si
Publisher version: https://doi.org/10.1021/acssuschemeng.8b02614
Appears in Collections:INV - AMIC - Artículos de Revistas
INV - MATCAT - Artículos de Revistas

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