CER - Central Repository
Institute of Chemistry, Technology and Metallurgy
    • English
    • Српски
    • Српски (Serbia)
  • English 
    • English
    • Serbian (Cyrilic)
    • Serbian (Latin)
  • Login
View Item 
  •   Central Repository
  • IHTM
  • Radovi istraživača / Researchers' publications
  • View Item
  •   Central Repository
  • IHTM
  • Radovi istraživača / Researchers' publications
  • View Item
JavaScript is disabled for your browser. Some features of this site may not work without it.

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

Thumbnail
2019
1-s2.0-S0277538719301664-main.pdf (1.377Mb)
Authors
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
Article (Accepted Version)
,
Elsevier
Metadata
Show full item record
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...itions.

Keywords:
Cu(II) complexes / hydrazones / DFT calculations / crystal structure / catalysis
Source:
Polyhedron, 2019, 165, 22-30
Publisher:
  • Elsevier
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)

DOI: 10.1016/j.poly.2019.03.001

ISSN: 0277-5387

WoS: 000471358500004

Scopus: 2-s2.0-85063237632
[ Google Scholar ]
8
8
URI
http://cer.ihtm.bg.ac.rs/handle/123456789/2632
Collections
  • Radovi istraživača / Researchers' publications
Institution
IHTM
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  - http://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",
url = "http://cer.ihtm.bg.ac.rs/handle/123456789/2632",
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 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. Polyhedron. 2019;165:22-30
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.
PolyhedronElsevier., 165, 22-30.
https://doi.org/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" 165 (2019):22-30,
https://doi.org/10.1016/j.poly.2019.03.001 .

DSpace software copyright © 2002-2015  DuraSpace
About CeR – Central Repository | Send Feedback

OpenAIRERCUB
 

 

All of DSpaceInstitutionsAuthorsTitlesSubjectsThis institutionAuthorsTitlesSubjects

Statistics

View Usage Statistics

DSpace software copyright © 2002-2015  DuraSpace
About CeR – Central Repository | Send Feedback

OpenAIRERCUB