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Nanopartículas de paladio soportadas en hidroxisales laminares: uso potencial en reacciones de Sonogashira
Palladium nanoparticles supported in laminar hydroxide salts: potential use in Sonogashira reactions
DOI:
https://doi.org/10.15446/rev.colomb.quim.v46n2.63028Palabras clave:
hidroxisales, lauril sulfato de sodio, paladio, acoplamiento C-C tipo Sonogashira, difenilacetileno, 2-fenilbenzofurano (es)hydroxide salts, sodium lauryl sulfate, palladium nanoparticles, Sonogashira C-C coupling reactions, diphenylacetylene, 2-phenylbenzofuran. (en)
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En este artículo se reporta la síntesis de nanopartículas de paladio soportadas en hidroxisales de acetato de zinc y modificadas con un surfactante (LHS-Zn-Ac/Pd0 y LHS-Zn-Suf/Pd0 respectivamente), mediante inserción de [PdCl4]2- y su posterior reducción con etanol en reflujo. Con la inserción de surfactante, la distancia interlaminar de la hidroxisal de partida (LHS-Zn-Ac) se incrementó de 13,8 Å a 29,8 Å, mientras que los materiales finales, que contenían paladio metálico registraron distancias interlaminares de 22,4 Å y 29,4 Å para LHS-Zn-Ac/Pd0 y LHS-Zn-Suf/Pd0 respectivamente. Las hidroxisales de acetato de zinc y de surfactante con nanopartículas metálicas de paladio incorporadas fueron ensayadas como potenciales catalizadores en la reacción de Sonogashira partiendo de fenilacetileno y yoduros de arilo, particularmente yodobenceno o 2-yodofenol, dando lugar a difenilacetileno (32% de rendimiento de producto aislado y purificado) o 2-fenilbenzofurano (18%). Todos los materiales inorgánicos fueron caracterizados mediante las siguientes técnicas: difracción de rayos X (XRD), microscopia electrónica de barrido (SEM y SEM-EDS), microscopia electrónica de transmisión (TEM) y espectroscopía de Infrarrojo con Transformada de Fourier (FT-IR). Por su parte los compuestos orgánicos se caracterizaron por resonancia magnética nuclear (1H-NMR y 13C-NMR) y cromatografía de gases acoplada a espectrometría de masas (GC-MS).
This article reports the synthesis of palladium nanoparticles supported on zinc acetate hydroxysalts and modified with a surfactant (LHS-Zn-Ac/Pd0 and LHS-Zn-Suf/Pd0 respectively), by insertion of tetrachloropaladate and its subsequent reduction with ethanol at reflux. With the surfactant insertion, the interlaminar distance of the starting hydroxysalt (LHS-Zn-Ac) increased from 13.8 Å to 29.8 Å, while the final materials containing palladium metal registered interlaminar distances of 22.4 Å and 29.4 Å for LHS-Zn-Ac/Pd0 and LHS-Zn-Suf/Pd0 respectively. Zinc acetate hydroxysalt and surfactant with incorporated palladium metal nanoparticles were tested as potential catalysts in the Sonogashira reaction starting from phenylacetylene and aryl iodides, particularly iodobenzene or 2-iodophenol, giving diphenylacetylene (32% yield of isolated and purified product) or 2-phenylbenzofuran (18%). All inorganic materials were characterized by the following techniques: (1) X-ray diffraction (XRD), (2) scanning electron microscopy (SEM and SEM-EDS), (3) transmission electron microscopy (TEM) and (4) Fourier transformed infrared spectroscopy (FT-IR). The organic compounds were characterized by nuclear magnetic resonance (1H-NMR and 13C-NMR) and gas chromatography coupled to mass spectrometry (GC-MS).
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Derechos de autor 2017 Cristian Camilo Giraldo Londoño, Rogelio Ocampo Cardona, Luz Amalia Ríos Vásquez, Maby Moll Martínez Garzón, Jhon Mauricio Aguirre Cortes
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