Tetrabutylphosphonium 4-ethoxyvalerate as a biomass-originated media for homogeneous palladium-catalyzed Hiyama coupling reactions
| Autor: | László T. Mika, József M. Tukacs, Ábrahám Papp, László Kollár, László Orha |
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| Rok vydání: | 2020 |
| Předmět: |
Chemistry
General Chemical Engineering Aryl chemistry.chemical_element General Chemistry Tetrabutylammonium fluoride Biochemistry Industrial and Manufacturing Engineering Catalysis Solvent chemistry.chemical_compound Homogeneous Ionic liquid Polymer chemistry Materials Chemistry Hiyama coupling Palladium |
| Zdroj: | Chemical Papers. 74:4593-4598 |
| ISSN: | 1336-9075 2585-7290 |
| DOI: | 10.1007/s11696-020-01287-y |
| Popis: | The introduction of a biomass-derived ionic liquid into the Hiyama coupling reactions, which has been considered as a powerful tool for the synthesis of symmetrically and non-symmetrically substituted biaryl structures, could further control or even reduce the environmental impact of this transformation. It was shown that tetrabutylphosphonium 4-ethoxyvalerate, a γ-valerolactone-based ionic liquid, can be utilized as an alternative solvent to create carbon–carbon bonds between aryl iodides and functionalized organosilanes in the presence of 1 mol% Pd under typical Hiyama conditions (130 °C, 24 h, tetrabutylammonium fluoride activator). A comparison of different ionic liquids was performed, and the effects of the catalyst precursor and the moisture content of the reaction mixture on the activity of the catalyst system were investigated. The functional group tolerance was also studied, resulting in 15 cross-coupling products (3a–o) with isolated yields of 45–72% and excellent purity (> 98%). |
| Databáze: | OpenAIRE |
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