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EnglishIn this contribution, we present a chemically efficient and sustainable protocol for the palladium-catalyzed copper-free Sonogashira cross-coupling reaction, based on the use of a heterogeneous catalytic system. This consists in the combination of a palladium catalyst on highly cross-linked thiazolidine network on silica and a polystyrene-supported base. The solid catalyst/base system acts as a palladium scavenger avoiding leaching of the metal and consequent product contamination. The reaction can be conducted in safe and easily recoverable acetonitrile/water azeotrope as reaction medium. This proved to be an efficient greener alternative to the classic toxic aprotic media commonly used in cross-coupling reaction, such as DMF and NMP. Acetonitrile/water azeotrope could be easily recovered and reused allowing the minimization of waste production. Our approach, based on the use of both a supported base and a supported catalyst, has proven to be efficient for the waste reduction, as proved by the low E-factor values achieved.
Kozell, V., Mclaughlin, M., Strappaveccia, G., Santoro, S., Bivona, L., Aprile, C., et al. (2016). Sustainable Approach to Waste-Minimized Sonogashira Cross-Coupling Reaction Based on Recoverable/Reusable Heterogeneous Catalytic/Base System and Acetonitrile Azeotrope. ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 4(12), 7209-7216 [10.1021/acssuschemeng.6b02170].
| Data di pubblicazione: | 2016 | |
| Titolo: | Sustainable Approach to Waste-Minimized Sonogashira Cross-Coupling Reaction Based on Recoverable/Reusable Heterogeneous Catalytic/Base System and Acetonitrile Azeotrope | |
| Autori: | ||
| Citazione: | Kozell, V., Mclaughlin, M., Strappaveccia, G., Santoro, S., Bivona, L., Aprile, C., et al. (2016). Sustainable Approach to Waste-Minimized Sonogashira Cross-Coupling Reaction Based on Recoverable/Reusable Heterogeneous Catalytic/Base System and Acetonitrile Azeotrope. ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 4(12), 7209-7216 [10.1021/acssuschemeng.6b02170]. | |
| Rivista: | ||
| Digital Object Identifier (DOI): | http://dx.doi.org/10.1021/acssuschemeng.6b02170 | |
| Abstract: | In this contribution, we present a chemically efficient and sustainable protocol for the palladium-catalyzed copper-free Sonogashira cross-coupling reaction, based on the use of a heterogeneous catalytic system. This consists in the combination of a palladium catalyst on highly cross-linked thiazolidine network on silica and a polystyrene-supported base. The solid catalyst/base system acts as a palladium scavenger avoiding leaching of the metal and consequent product contamination. The reaction can be conducted in safe and easily recoverable acetonitrile/water azeotrope as reaction medium. This proved to be an efficient greener alternative to the classic toxic aprotic media commonly used in cross-coupling reaction, such as DMF and NMP. Acetonitrile/water azeotrope could be easily recovered and reused allowing the minimization of waste production. Our approach, based on the use of both a supported base and a supported catalyst, has proven to be efficient for the waste reduction, as proved by the low E-factor values achieved. | |
| URL: | http://pubs.acs.org/journal/ascecg | |
| Settore Scientifico Disciplinare: | Settore CHIM/06 - Chimica Organica | |
| Appare nelle tipologie: | 1.01 Articolo in rivista |
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| ACS Sustainable Chem Eng 2016, 4, 7209.pdf | Articolo principale | Versione Editoriale | Administrator Richiedi una copia |
http://hdl.handle.net/10447/220024
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