Thiol-yne click reaction: an interesting way to derive thiol-provided catechols
| Autor: | Daniel Ruiz-Molina, Fabiana Nador, Duham Zanotto, Juan Mancebo-Aracil, Gabriel Radivoy |
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| Přispěvatelé: | Agencia Nacional de Promoción Científica y Tecnológica (Argentina), Consejo Nacional de Investigaciones Científicas y Técnicas (Argentina), Secretaría de Ciencia y Técnica de la Nación (Argentina), Universidad Nacional del Sur |
| Rok vydání: | 2021 |
| Předmět: |
chemistry.chemical_classification
Catechol Propiolic acid Coordination polymer General Chemical Engineering 2-ethynylpyridine 1 2-dichloroethanes Coordination Polymers General Chemistry Heterogeneous catalysis Combinatorial chemistry Heterogeneous catalyst Catalysis chemistry.chemical_compound Catechol derivatives Michael additions chemistry Michael reaction Click chemistry Thiol Copper nanoparticles Coordination sites |
| Zdroj: | Dipòsit Digital de Documents de la UAB Universitat Autònoma de Barcelona Digital.CSIC. Repositorio Institucional del CSIC instname |
| ISSN: | 2046-2069 |
| Popis: | 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. This work was supported by the ANPCyT (Project PICT 2016-0385), SGCyT-UNS (Project PGI 24/Q106) and CONICET (Project PIP 11220130100498CO). |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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