Highly-efficient N-arylation of imidazole catalyzed by Cu(II) complexes with quaternary ammonium-functionalized 2-acetylpyridine acylhydrazone
Само за регистроване кориснике
2019
Аутори
Milenković, Milica R.Papastavrou, Agyro T.
Radanović, Dušanka D.
Pevec, Andrej
Jagličić, Zvonko
Zlatar, Matija
Gruden-Pavlović, Maja
Vougioukalakis, Georgios C.
Turel, Iztok
Anđelković, Katarina K.
Čobeljić, Božidar
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
The reaction of (E)-N,N,N-trimethyl-2-oxo-2-(2-(1-(pyridin-2-yl)ethylidene)hydrazinyl)ethan-1-aminium-chloride (HLCl) with copper(II) perchlorate led to mononuclear [CuLCl]ClO 4 complex (1). The same reaction with excess of sodium azide gives dinuclear azido double end-on bridged Cu(II) complex [Cu 2 L 2 (μ- 1,1 -N 3 ) 2 ](ClO 4 ) 2 (2). In both complexes hydrazone ligand is NNO coordinated in monodeprotonated formally neutral zwitter-ionic form. Complexes were characterized by elemental analysis, IR spectroscopy and single-crystal X-ray crystallography. Variable‐temperature magnetic susceptibility measurements for dinuclear Cu(II) complex showed intra-dimer ferromagnetic coupling between Cu(II) ions (J = 7.4 cm −1 ). DFT-BS calculations provided explanation for magnetic properties of dinuclear Cu(II) complex. Both complexes were shown to highly efficiently catalyze the N-arylation of imidazole and benzimidazole with electron-poor or electron-rich aryl iodides, under user-friendly and ...sustainable conditions.
Кључне речи:
Catalysis / Crystal structure / Cu(II) complexes / DFT calculations / HydrazonesИзвор:
Polyhedron, 2019, 165, 22-30Издавач:
- Elsevier
Финансирање / пројекти:
- Интеракције природних производа, њихових деривата и комплексних једињења са протеинима и нуклеинским киселинама (RS-MESTD-Basic Research (BR or ON)-172055)
- Slovenian Research Agency (P-0175 and P2-0348)
- COST Action CA15106 (C-H Activation in Organic Synthesis – CHAOS)
- Special Account for Research Grants of the National and Kapodistrian University of Athens (Research Program 70/3/14872)
Напомена:
- Peer-reviewed manuscript: http://cherry.chem.bg.ac.rs/handle/123456789/2865
- Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/3006
DOI: 10.1016/j.poly.2019.03.001
ISSN: 0277-5387
WoS: 000471358500004
Scopus: 2-s2.0-85063237632
Колекције
Институција/група
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Milenković, Milica R. AU - Papastavrou, Agyro T. AU - Radanović, Dušanka D. AU - Pevec, Andrej AU - Jagličić, Zvonko AU - Zlatar, Matija AU - Gruden-Pavlović, Maja AU - Vougioukalakis, Georgios C. AU - Turel, Iztok AU - Anđelković, Katarina K. AU - Čobeljić, Božidar PY - 2019 UR - https://cherry.chem.bg.ac.rs/handle/123456789/2858 AB - The reaction of (E)-N,N,N-trimethyl-2-oxo-2-(2-(1-(pyridin-2-yl)ethylidene)hydrazinyl)ethan-1-aminium-chloride (HLCl) with copper(II) perchlorate led to mononuclear [CuLCl]ClO 4 complex (1). The same reaction with excess of sodium azide gives dinuclear azido double end-on bridged Cu(II) complex [Cu 2 L 2 (μ- 1,1 -N 3 ) 2 ](ClO 4 ) 2 (2). In both complexes hydrazone ligand is NNO coordinated in monodeprotonated formally neutral zwitter-ionic form. Complexes were characterized by elemental analysis, IR spectroscopy and single-crystal X-ray crystallography. Variable‐temperature magnetic susceptibility measurements for dinuclear Cu(II) complex showed intra-dimer ferromagnetic coupling between Cu(II) ions (J = 7.4 cm −1 ). DFT-BS calculations provided explanation for magnetic properties of dinuclear Cu(II) complex. Both complexes were shown to highly efficiently catalyze the N-arylation of imidazole and benzimidazole with electron-poor or electron-rich aryl iodides, under user-friendly and sustainable conditions. PB - Elsevier T2 - Polyhedron T1 - Highly-efficient N-arylation of imidazole catalyzed by Cu(II) complexes with quaternary ammonium-functionalized 2-acetylpyridine acylhydrazone VL - 165 SP - 22 EP - 30 DO - 10.1016/j.poly.2019.03.001 ER -
@article{ author = "Milenković, Milica R. and Papastavrou, Agyro T. and Radanović, Dušanka D. and Pevec, Andrej and Jagličić, Zvonko and Zlatar, Matija and Gruden-Pavlović, Maja and Vougioukalakis, Georgios C. and Turel, Iztok and Anđelković, Katarina K. and Čobeljić, Božidar", year = "2019", abstract = "The reaction of (E)-N,N,N-trimethyl-2-oxo-2-(2-(1-(pyridin-2-yl)ethylidene)hydrazinyl)ethan-1-aminium-chloride (HLCl) with copper(II) perchlorate led to mononuclear [CuLCl]ClO 4 complex (1). The same reaction with excess of sodium azide gives dinuclear azido double end-on bridged Cu(II) complex [Cu 2 L 2 (μ- 1,1 -N 3 ) 2 ](ClO 4 ) 2 (2). In both complexes hydrazone ligand is NNO coordinated in monodeprotonated formally neutral zwitter-ionic form. Complexes were characterized by elemental analysis, IR spectroscopy and single-crystal X-ray crystallography. Variable‐temperature magnetic susceptibility measurements for dinuclear Cu(II) complex showed intra-dimer ferromagnetic coupling between Cu(II) ions (J = 7.4 cm −1 ). DFT-BS calculations provided explanation for magnetic properties of dinuclear Cu(II) complex. Both complexes were shown to highly efficiently catalyze the N-arylation of imidazole and benzimidazole with electron-poor or electron-rich aryl iodides, under user-friendly and sustainable conditions.", publisher = "Elsevier", journal = "Polyhedron", title = "Highly-efficient N-arylation of imidazole catalyzed by Cu(II) complexes with quaternary ammonium-functionalized 2-acetylpyridine acylhydrazone", volume = "165", pages = "22-30", doi = "10.1016/j.poly.2019.03.001" }
Milenković, M. R., Papastavrou, A. T., Radanović, D. D., Pevec, A., Jagličić, Z., Zlatar, M., Gruden-Pavlović, M., Vougioukalakis, G. C., Turel, I., Anđelković, K. K.,& Čobeljić, B.. (2019). Highly-efficient N-arylation of imidazole catalyzed by Cu(II) complexes with quaternary ammonium-functionalized 2-acetylpyridine acylhydrazone. in Polyhedron Elsevier., 165, 22-30. https://doi.org/10.1016/j.poly.2019.03.001
Milenković MR, Papastavrou AT, Radanović DD, Pevec A, Jagličić Z, Zlatar M, Gruden-Pavlović M, Vougioukalakis GC, Turel I, Anđelković KK, Čobeljić B. Highly-efficient N-arylation of imidazole catalyzed by Cu(II) complexes with quaternary ammonium-functionalized 2-acetylpyridine acylhydrazone. in Polyhedron. 2019;165:22-30. doi:10.1016/j.poly.2019.03.001 .
Milenković, Milica R., Papastavrou, Agyro T., Radanović, Dušanka D., Pevec, Andrej, Jagličić, Zvonko, Zlatar, Matija, Gruden-Pavlović, Maja, Vougioukalakis, Georgios C., Turel, Iztok, Anđelković, Katarina K., Čobeljić, Božidar, "Highly-efficient N-arylation of imidazole catalyzed by Cu(II) complexes with quaternary ammonium-functionalized 2-acetylpyridine acylhydrazone" in Polyhedron, 165 (2019):22-30, https://doi.org/10.1016/j.poly.2019.03.001 . .