Multilayer graphene functionalized through thermal 1,3-dipolar cycloadditions with imino esters: a versatile platform for supported ligands in catalysis

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Title: Multilayer graphene functionalized through thermal 1,3-dipolar cycloadditions with imino esters: a versatile platform for supported ligands in catalysis
Authors: Ferrándiz-Saperas, Marcos | Ghisolfi, Alessio | Cazorla-Amorós, Diego | Nájera, Carmen | Sansano, Jose M.
Research Group/s: Materiales Carbonosos y Medio Ambiente | Síntesis Asimétrica (SINTAS)
Center, Department or Service: Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Departamento de Química Inorgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica | Universidad de Alicante. Instituto Universitario de Materiales
Keywords: Multilayer graphene | 1,3-dipolar cycloadditions | Imino esters | Ligands | Catalysis
Knowledge Area: Química Orgánica | Química Inorgánica
Issue Date: 3-Jun-2019
Publisher: Royal Society of Chemistry
Citation: Chemical Communications. 2019, 55: 7462-7465. doi:10.1039/c9cc00939f
Abstract: Multilayer graphene (MLG), obtained by mild sonication of graphite in NMP or pyridine, was fully characterized via atomic force microscopy (AFM), transmission electron microscopy (TEM), Raman spectroscopy and X-ray photoemission spectroscopy (XPS). Then, it was functionalized via 1,3-dipolar cycloaddition with azomethine ylides generated by thermal 1,2-prototropy of various imino esters. The resulting MLG, containing substituted proline-based amine functions, was characterized by XPS and it showed high nitrogen loading, ranging from 0.6 to 4.2 at% depending on the imino ester used. Among these functionalized MLGs a probe sample was subjected to ester hydrolysis and used as a heterogeneous N,O-chelating ligand to coordinate iridium atomic centers. This supported complex was also characterized by XPS and its catalytic activity was tested in the hydrogen transfer reduction of acetophenone, obtaining up to 85% yield. Furthermore, this catalyst could be recycled up to four times.
Sponsor: We gratefully acknowledge financial support from the Spanish Ministerio de Economía y Competitividad (MINECO) (projects CTQ2013-43446-P, RTI2018-095291-B-I00 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 CTQ2015-66080-R, CTQ2016-76782-P and CTQ2016-81797-REDC), the Generalitat Valenciana (PROMETEOII/2014/017) and the University of Alicante.
ISSN: 1359-7345 (Print) | 1364-548X (Online)
DOI: 10.1039/c9cc00939f
Language: eng
Type: info:eu-repo/semantics/article
Rights: © The Royal Society of Chemistry 2019
Peer Review: si
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Appears in Collections:INV - MCMA - Artículos de Revistas
INV - SINTAS - Artículos de Revistas

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