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

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

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]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...

Keywords:

Cu(II) complexes / hydrazones / DFT calculations / crystal structure / catalysis

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)

Note:

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

Related info:

Version of
https://cer.ihtm.bg.ac.rs/handle/123456789/2632
Referenced by
https://cer.ihtm.bg.ac.rs/handle/123456789/4472
Referenced by
https://cer.ihtm.bg.ac.rs/handle/123456789/4473
Referenced by
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

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TY  - 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 . .