Thiol-yne click reaction : an interesting way to derive thiol-provided catechols
Nador, Fabiana (Institut Català de Nanociència i Nanotecnologia)
Mancebo Aracil, Juan (Universidad Nacional del Sur. Instituto de Química del Sur)
Zanotto, Duham (Universidad Nacional del Sur. Instituto de Química del Sur)
Ruiz-Molina, Daniel (Institut Català de Nanociència i Nanotecnologia)
Radivoy, Gabriel (Universidad Nacional del Sur. Instituto de Química del Sur)

Data:	2021
Resum:	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.
Nota:	Ajuts: this work was supported by the ANPCyT (Project PICT 2016-0385), SGCyT-UNS (Project PGI 24/Q106) and CONICET (Project PIP 11220130100498CO). We thank Belén Ballesteros and Marcos Rosado from Electron Microscopy Unit of Institut Català de Nanociència i Nanotecnologia (ICN2) in Barcelona, Spain; and Maria Julia Yañez from Electron Microscopy Unit in Centro Científico Tecnológico - CONICET, Bahía Blanca, Argentina for their measurements and assistance. We thank Miguel Ángel Moreno-Villaécija for carrying out the ICP/MS analysis.
Drets:	Aquest document està subjecte a una llicència d'ús Creative Commons. Es permet la reproducció total o parcial, la distribució, la comunicació pública de l'obra i la creació d'obres derivades, sempre que no sigui amb finalitats comercials, i sempre que es reconegui l'autoria de l'obra original.
Llengua:	Anglès
Document:	Article ; recerca ; Versió publicada
Matèria:	1,2-dichloroethanes ; 2-ethynylpyridine ; Catechol derivatives ; Coordination Polymers ; Coordination sites ; Copper nanoparticles ; Heterogeneous catalyst ; Michael additions
Publicat a:	RSC advances, Vol. 11, issue 4 (2021) , p. 2074-2082, ISSN 2046-2069

DOI: 10.1039/d0ra09687c
PMID: 35424146

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