COST Action CA15106 (C-H Activation in Organic Synthesis –CHAOS)

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COST Action CA15106 (C-H Activation in Organic Synthesis –CHAOS)

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Publications

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

(Elsevier, 2019)

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/123456789/2632
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 . .
1
16
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17

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

(Elsevier, 2019)

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 . .
1
16
13
17

Supplementary material for: "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

(Elsevier, 2019)

TY  - DATA
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/123456789/4472
AB  - Table S1. Hydrogen-bond parameters for complexes 1 and 2. Fig. S1. Packing diagram of 1. Fig. S2. Crystal packing of 2. Table S2 Influence of the exchange-correlation functional and basis set on the calculated exchange coupling constant J.
PB  - Elsevier
T2  - Polyhedron
T1  - Supplementary material for: "Highly-efficient N-arylation of imidazole catalyzed by Cu(II) complexes with quaternary ammonium-functionalized 2-acetylpyridine acylhydrazone"
UR  - https://hdl.handle.net/21.15107/rcub_cer_4472
ER  - 
@misc{
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 = "Table S1. Hydrogen-bond parameters for complexes 1 and 2. Fig. S1. Packing diagram of 1. Fig. S2. Crystal packing of 2. Table S2 Influence of the exchange-correlation functional and basis set on the calculated exchange coupling constant J.",
publisher = "Elsevier",
journal = "Polyhedron",
title = "Supplementary material for: "Highly-efficient N-arylation of imidazole catalyzed by Cu(II) complexes with quaternary ammonium-functionalized 2-acetylpyridine acylhydrazone"",
url = "https://hdl.handle.net/21.15107/rcub_cer_4472"
}
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). Supplementary material for: "Highly-efficient N-arylation of imidazole catalyzed by Cu(II) complexes with quaternary ammonium-functionalized 2-acetylpyridine acylhydrazone". in Polyhedron
Elsevier..
https://hdl.handle.net/21.15107/rcub_cer_4472
Milenković MR, Papastavrou AT, Radanović D, Pevec A, Jagličić Z, Zlatar M, Gruden M, Vougioukalakis GC, Turel I, Anđelković K, Čobeljić B. Supplementary material for: "Highly-efficient N-arylation of imidazole catalyzed by Cu(II) complexes with quaternary ammonium-functionalized 2-acetylpyridine acylhydrazone". in Polyhedron. 2019;.
https://hdl.handle.net/21.15107/rcub_cer_4472 .
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, "Supplementary material for: "Highly-efficient N-arylation of imidazole catalyzed by Cu(II) complexes with quaternary ammonium-functionalized 2-acetylpyridine acylhydrazone"" in Polyhedron (2019),
https://hdl.handle.net/21.15107/rcub_cer_4472 .

CCDC 1886534: Experimental Crystal Structure Determination. Crystallographic data for: "Highly-efficient N-arylation of imidazole catalyzed by Cu(II) complexes with quaternary ammonium-functionalized 2-acetylpyridine acylhydrazone"

Pevec, Andrej

(The Cambridge Crystallographic Data Centre (CCDC), 2019)

TY  - DATA
AU  - Pevec, Andrej
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4473
AB  - HIYYAS : chloro-[2-(oxy)-N,N,N-trimethyl-2-{[1-(pyridin-2-yl)ethylidene]hydrazinylidene}ethan-1-aminiumato]-perchlorato-copper(ii) Space Group: P 21/c (14), Cell: a 9.9406(2)Å b 9.5650(2)Å c 18.8796(5)Å, α 90° β 94.7120(10)° γ 90°
PB  - The Cambridge Crystallographic Data Centre (CCDC)
T1  - CCDC 1886534: Experimental Crystal Structure Determination. Crystallographic data for: "Highly-efficient N-arylation of imidazole catalyzed by Cu(II) complexes with quaternary ammonium-functionalized 2-acetylpyridine acylhydrazone"
DO  - 10.5517/ccdc.csd.cc21b2yf
ER  - 
@misc{
author = "Pevec, Andrej",
year = "2019",
abstract = "HIYYAS : chloro-[2-(oxy)-N,N,N-trimethyl-2-{[1-(pyridin-2-yl)ethylidene]hydrazinylidene}ethan-1-aminiumato]-perchlorato-copper(ii) Space Group: P 21/c (14), Cell: a 9.9406(2)Å b 9.5650(2)Å c 18.8796(5)Å, α 90° β 94.7120(10)° γ 90°",
publisher = "The Cambridge Crystallographic Data Centre (CCDC)",
title = "CCDC 1886534: Experimental Crystal Structure Determination. Crystallographic data for: "Highly-efficient N-arylation of imidazole catalyzed by Cu(II) complexes with quaternary ammonium-functionalized 2-acetylpyridine acylhydrazone"",
doi = "10.5517/ccdc.csd.cc21b2yf"
}
Pevec, A.. (2019). CCDC 1886534: Experimental Crystal Structure Determination. Crystallographic data for: "Highly-efficient N-arylation of imidazole catalyzed by Cu(II) complexes with quaternary ammonium-functionalized 2-acetylpyridine acylhydrazone". 
The Cambridge Crystallographic Data Centre (CCDC)..
https://doi.org/10.5517/ccdc.csd.cc21b2yf
Pevec A. CCDC 1886534: Experimental Crystal Structure Determination. Crystallographic data for: "Highly-efficient N-arylation of imidazole catalyzed by Cu(II) complexes with quaternary ammonium-functionalized 2-acetylpyridine acylhydrazone". 2019;.
doi:10.5517/ccdc.csd.cc21b2yf .
Pevec, Andrej, "CCDC 1886534: Experimental Crystal Structure Determination. Crystallographic data for: "Highly-efficient N-arylation of imidazole catalyzed by Cu(II) complexes with quaternary ammonium-functionalized 2-acetylpyridine acylhydrazone"" (2019),
https://doi.org/10.5517/ccdc.csd.cc21b2yf . .

CCDC 1886535: Experimental Crystal Structure Determination. Crystallographic data for: "Highly-efficient N-arylation of imidazole catalyzed by Cu(II) complexes with quaternary ammonium-functionalized 2-acetylpyridine acylhydrazone"

Pevec, Andrej

(The Cambridge Crystallographic Data Centre (CCDC), 2019)

TY  - DATA
AU  - Pevec, Andrej
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4474
AB  - HIYYEW : bis(μ-azido)-bis[2-(oxy)-N,N,N-trimethyl-2-{[1-(pyridin-2-yl)ethylidene]hydrazinylidene}ethan-1-aminiumato]-di-copper(ii) bis(perchlorate) Space Group: C 2/c (15), Cell: a 16.4095(6)Å b 13.6320(6)Å c 17.1507(8)Å, α 90° β 108.145(5)° γ 90°
PB  - The Cambridge Crystallographic Data Centre (CCDC)
T1  - CCDC 1886535: Experimental Crystal Structure Determination. Crystallographic data for: "Highly-efficient N-arylation of imidazole catalyzed by Cu(II) complexes with quaternary ammonium-functionalized 2-acetylpyridine acylhydrazone"
DO  - 10.5517/ccdc.csd.cc21b2zg
ER  - 
@misc{
author = "Pevec, Andrej",
year = "2019",
abstract = "HIYYEW : bis(μ-azido)-bis[2-(oxy)-N,N,N-trimethyl-2-{[1-(pyridin-2-yl)ethylidene]hydrazinylidene}ethan-1-aminiumato]-di-copper(ii) bis(perchlorate) Space Group: C 2/c (15), Cell: a 16.4095(6)Å b 13.6320(6)Å c 17.1507(8)Å, α 90° β 108.145(5)° γ 90°",
publisher = "The Cambridge Crystallographic Data Centre (CCDC)",
title = "CCDC 1886535: Experimental Crystal Structure Determination. Crystallographic data for: "Highly-efficient N-arylation of imidazole catalyzed by Cu(II) complexes with quaternary ammonium-functionalized 2-acetylpyridine acylhydrazone"",
doi = "10.5517/ccdc.csd.cc21b2zg"
}
Pevec, A.. (2019). CCDC 1886535: Experimental Crystal Structure Determination. Crystallographic data for: "Highly-efficient N-arylation of imidazole catalyzed by Cu(II) complexes with quaternary ammonium-functionalized 2-acetylpyridine acylhydrazone". 
The Cambridge Crystallographic Data Centre (CCDC)..
https://doi.org/10.5517/ccdc.csd.cc21b2zg
Pevec A. CCDC 1886535: Experimental Crystal Structure Determination. Crystallographic data for: "Highly-efficient N-arylation of imidazole catalyzed by Cu(II) complexes with quaternary ammonium-functionalized 2-acetylpyridine acylhydrazone". 2019;.
doi:10.5517/ccdc.csd.cc21b2zg .
Pevec, Andrej, "CCDC 1886535: Experimental Crystal Structure Determination. Crystallographic data for: "Highly-efficient N-arylation of imidazole catalyzed by Cu(II) complexes with quaternary ammonium-functionalized 2-acetylpyridine acylhydrazone"" (2019),
https://doi.org/10.5517/ccdc.csd.cc21b2zg . .