Highly-efficient N-arylation of imidazole catalyzed by Cu(II) complexes with quaternary ammonium-functionalized 2-acetylpyridine acylhydrazone

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

doi:10.1016/j.poly.2019.03.001

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2019

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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 ...

Keywords:

Catalysis / Crystal structure / Cu(II) complexes / DFT calculations / Hydrazones

Source:
Polyhedron, 2019, 165, 22-30

Publisher:

Elsevier

Funding / projects:

Interactions of natural products, their derivatives and coordination compounds with proteins and nucleic acids (RS-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)

Note:

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

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TY  - 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 . .