1,3‐Dipolar Cycloadditions of Stabilized Azomethine Ylides and Electrophilic Alkenes Mediated by a Recyclable TSIL·AgOAc Catalyst

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Title: 1,3‐Dipolar Cycloadditions of Stabilized Azomethine Ylides and Electrophilic Alkenes Mediated by a Recyclable TSIL·AgOAc Catalyst
Authors: Lledó, David | Grindlay, Guillermo | Sansano, Jose M.
Research Group/s: Espectrometría Atómica Analítica (GEAA) | Síntesis Asimétrica (SINTAS)
Center, Department or Service: Universidad de Alicante. Departamento de Química Analítica, Nutrición y Bromatología | Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica
Keywords: Cycloaddition | Green chemistry | Ionic liquids | Silver | Ylides
Knowledge Area: Química Analítica | Química Orgánica
Issue Date: 7-Jul-2019
Publisher: Wiley-VCH Verlag GmbH & Co. KGaA
Citation: European Journal of Organic Chemistry. 2019, 25: 4095-4100. doi:10.1002/ejoc.201900724
Abstract: The synthesis of a task‐specific ionic liquid (TSIL) based on a BMIM ionic liquid phosphane is achieved by modification of the original procedure. It is used as a ligand with AgOAc, and the resulting complex is fully characterized. This catalytic system promotes the 1,3‐dipolar cycloaddition of stabilized azomethine ylides and electrophilic alkenes using a green methodology. The green character was analyzed using an overall set of parameters finding the optimal conditions and individualized separation/purification methods for each cycloadduct. The determination of the most important green metrics is reported in this survey, demonstrating the value of this methodology on a laboratory scale or even at an industrial level.
Sponsor: We gratefully acknowledge financial support from the Spanish Ministerio de Ciencia, Innovación y Universidades (projects CTQ2013-43446-P, CTQ2016-81893REDT and CTQ2014-51912-REDC) the Spanish Ministerio de Economía, Industria y Competitividad, Agencia Estatal de Investigación (AEI) and Fondo Europeo de Desarrollo Regional (FEDER, EU) (projects CTQ2016-76782-P, CTQ2016-80375-P and CTQ2016-81797-REDC), the Generalitat Valenciana (PROMETEOII/2014/017), and the University of Alicante. D. Lledó thanks the Spanish Ministerio de Educación for the given fellowship FPU15/00097.
URI: http://hdl.handle.net/10045/93808
ISSN: 1434-193X (Print) | 1099-0690 (Online)
DOI: 10.1002/ejoc.201900724
Language: eng
Type: info:eu-repo/semantics/article
Rights: © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Peer Review: si
Publisher version: https://doi.org/10.1002/ejoc.201900724
Appears in Collections:INV - SINTAS - Artículos de Revistas
INV - GEAA - Artículos de Revistas

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