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, Argyro T.
Radanović, Dušanka
Pevec, Andrej
Jagličić, Zvonko
Zlatar, Matija
Gruden, Maja
Vougioukalakis, Georgios C.
Turel, Iztok
Anđelković, Katarina
Čobeljić, Božidar
Чланак у часопису (Објављена верзија)
,
Elsevier
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]ClO4 complex (1). The same reaction with excess of sodium azide gives dinuclear azido double end-on bridged Cu(II) complex [Cu2L2(μ-1,1-N3)2](ClO4)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 cond...itions.
Кључне речи:
Cu(II) complexes / hydrazones / DFT calculations / crystal structure / catalysisИзвор:
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)
Напомена:
- Peer-reviewed manuscript: http://cer.ihtm.bg.ac.rs/handle/123456789/2632
- Supplementary material: https://cer.ihtm.bg.ac.rs/handle/123456789/4472
- Crystallographic data (CCDC 1886534): https://cer.ihtm.bg.ac.rs/handle/123456789/4473
- Crystallographic data (CCDC 1886535): https://cer.ihtm.bg.ac.rs/handle/123456789/4474
Повезане информације:
- Друга верзија
https://cer.ihtm.bg.ac.rs/handle/123456789/2632 - Повезани садржај
https://cer.ihtm.bg.ac.rs/handle/123456789/4472 - Повезани садржај
https://cer.ihtm.bg.ac.rs/handle/123456789/4473 - Повезани садржај
https://cer.ihtm.bg.ac.rs/handle/123456789/4474
DOI: 10.1016/j.poly.2019.03.001
ISSN: 0277-5387
WoS: 000471358500004
Scopus: 2-s2.0-85063237632
Институција/група
IHTMTY - JOUR AU - Milenković, Milica R. AU - Papastavrou, Argyro T. AU - Radanović, Dušanka AU - Pevec, Andrej AU - Jagličić, Zvonko AU - Zlatar, Matija AU - Gruden, Maja AU - Vougioukalakis, Georgios C. AU - Turel, Iztok AU - Anđelković, Katarina AU - Čobeljić, Božidar PY - 2019 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/2634 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]ClO4 complex (1). The same reaction with excess of sodium azide gives dinuclear azido double end-on bridged Cu(II) complex [Cu2L2(μ-1,1-N3)2](ClO4)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, Argyro T. and Radanović, Dušanka and Pevec, Andrej and Jagličić, Zvonko and Zlatar, Matija and Gruden, Maja and Vougioukalakis, Georgios C. and Turel, Iztok and Anđelković, Katarina 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]ClO4 complex (1). The same reaction with excess of sodium azide gives dinuclear azido double end-on bridged Cu(II) complex [Cu2L2(μ-1,1-N3)2](ClO4)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., Pevec, A., Jagličić, Z., Zlatar, M., Gruden, M., Vougioukalakis, G. C., Turel, I., Anđelković, 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 D, Pevec A, Jagličić Z, Zlatar M, Gruden M, Vougioukalakis GC, Turel I, Anđelković K, 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, Argyro T., Radanović, Dušanka, Pevec, Andrej, Jagličić, Zvonko, Zlatar, Matija, Gruden, Maja, Vougioukalakis, Georgios C., Turel, Iztok, Anđelković, Katarina, 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 . .