Solvent-free copper-catalyzed click chemistry for the synthesis of N-heterocyclic hybrids based on quinoline and 1,2,3-triazole
| Autor: | Mario Cetina, Krunoslav Užarević, Martina Tireli, Stipe Lukin, Marina Juribašić Kulcsar, Ivan Halasz, Dijana Žilić, Silvana Raić-Malić, Silvija Maračić |
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| Jazyk: | angličtina |
| Rok vydání: | 2017 |
| Předmět: |
Inorganic chemistry
chemistry.chemical_element 010402 general chemistry electron spin resonance (ESR) spectroscopy 01 natural sciences Catalysis lcsh:QD241-441 chemistry.chemical_compound lcsh:Organic chemistry Mechanochemistry quinoline Reactivity (chemistry) lcsh:Science 010405 organic chemistry Organic Chemistry Quinoline Copper 0104 chemical sciences Chemistry chemistry quinolone click chemistry mechanochemistry Raman monitoring Electron spin resonance (ESR) spectroscopy solid-state click chemistry Yield (chemistry) Click chemistry in situ Raman monitoring lcsh:Q Azide |
| Zdroj: | Beilstein Journal of Organic Chemistry, Vol 13, Iss 1, Pp 2352-2363 (2017) Beilstein Journal of Organic Chemistry |
| ISSN: | 1860-5397 |
| Popis: | Copper-catalyzed mechanochemical click reactions using Cu(II), Cu(I) and Cu(0) catalysts have been successfully implemented to provide novel 6-phenyl-2-(trifluoromethyl)quinolines with a phenyl-1,2,3-triazole moiety at O-4 of the quinoline core. Milling procedures proved to be significantly more efficient than the corresponding solution reactions, with up to a 15-fold gain in yield. Efficiency of both solution and milling procedures depended on the p-substituent in the azide reactant, resulting in H < Cl < Br < I reactivity bias. Solid-state catalysis using Cu(II) and Cu(I) catalysts entailed the direct involvement of the copper species in the reaction and generation of highly luminescent compounds which hindered in situ monitoring by Raman spectroscopy. However, in situ monitoring of the milling processes was enabled by using Cu(0) catalysts in the form of brass milling media which offered a direct insight into the reaction pathway of mechanochemical CuAAC reactions, indicating that the catalysis is most likely conducted on the surface of milling balls. Electron spin resonance spectroscopy was used to determine the oxidation and spin states of the respective copper catalysts in bulk products obtained by milling procedures. |
| Databáze: | OpenAIRE |
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