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 |
Files in This Item:
| File | Description | Size | Format | |
|---|---|---|---|---|
 2019_Lledo_etal_EurJOC_final.pdf | Versión final (acceso restringido) | 950,13 kB | Adobe PDF | Open Request a copy |
 2019_Lledo_etal_EurJOC_accepted.pdf | Accepted Manuscript (acceso abierto) | 1,42 MB | Adobe PDF | Open Preview |
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