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Artículo

Thiol-yne click reaction: an interesting way to derive thiol-provided catechols

Nador, Fabiana GabrielaIcon ; Mancebo Aracil, JuanIcon ; Ruiz Molina, Daniel; Radivoy, Gabriel EduardoIcon
Fecha de publicación: 07/01/2021
Editorial: Royal Society of Chemistry
Revista: RSC Advances
ISSN: 2046-2069
Idioma: Inglés
Tipo de recurso: Artículo publicado
Clasificación temática:
Química Orgánica

Resumen

The hydrothiolation of activated alkynes is presented as an attractive and powerful way to functionalize thiols bearing catechols. The reaction was promoted by a heterogeneous catalyst composed of copper nanoparticles supported on TiO2 (CuNPs/TiO2) in 1,2-dichloroethane (1,2-DCE) under heating at 80 °C. The catalyst could be recovered and reused in three consecutive cycles, showing a slight decrease in its catalytic activity. Thiol derivatives bearing catechol moieties, obtained through a versatile Michael addition, were reacted with different activated alkynes, such as methyl propiolate, propiolic acid, propiolamide or 2-ethynylpyridine. The reaction was shown to be regio- and stereoselective towards anti-Markovnikov Z-vinyl sulfide in most cases studied. Finally, some catechol derivatives obtained were tested as ligands in the preparation of coordination polymer nanoparticles (CNPs), by taking the advantage of their different coordination sites with metals such as iron and cobalt.
Palabras clave: CATECHOL , THIOL-YNE , VINYL SULFIDE
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info:eu-repo/semantics/openAccess Excepto donde se diga explícitamente, este item se publica bajo la siguiente descripción: Creative Commons Attribution-NonCommercial 2.5 Unported (CC BY-NC 2.5)
Identificadores
URI: http://hdl.handle.net/11336/166630
DOI: https://doi.org/10.1039/D0RA09687C
URL: https://pubs.rsc.org/en/content/articlelanding/2021/RA/D0RA09687C
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Articulos(INQUISUR)
Articulos de INST.DE QUIMICA DEL SUR
Citación
Nador, Fabiana Gabriela; Mancebo Aracil, Juan; No especifica; Ruiz Molina, Daniel; Radivoy, Gabriel Eduardo; Thiol-yne click reaction: an interesting way to derive thiol-provided catechols; Royal Society of Chemistry; RSC Advances; 11; 4; 7-1-2021; 2074-2082
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