Highly-efficient N-arylation of imidazole catalyzed by Cu(II) complexes with quaternary ammonium-functionalized 2-acetylpyridine acylhydrazone
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AuthorsMilenković, Milica R.
Papastavrou, Argyro T.
Vougioukalakis, Georgios C.
Article (Published version)
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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
- 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)
- Peer-reviewed manuscript: http://cer.ihtm.bg.ac.rs/handle/123456789/2632