Solvent-free copper-catalyzed click chemistry for the synthesis of N-heterocyclic hybrids based on quinoline and 1,2,3-triazole
Science
Electron spin resonance (ESR) spectroscopy
Q
Organic chemistry
electron spin resonance (ESR) spectroscopy
01 natural sciences
Full Research Paper
0104 chemical sciences
3. Good health
Raman monitoring
Chemistry
QD241-441
quinolone
solid-state click chemistry
quinolone ; click chemistry ; mechanochemistry ; Raman monitoring ; Electron spin resonance (ESR) spectroscopy
13. Climate action
quinoline
click chemistry
in situ Raman monitoring
mechanochemistry
DOI:
10.3762/bjoc.13.232
Publication Date:
2017-11-06T09:58:13Z
AUTHORS (9)
ABSTRACT
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.
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