Synthesis and properties of heteroaromatic carbenes of the imidazole and triazole series and their fused analogues

Коротких, Н. И.; Cowley, Alan H.; Clyburne, Jason A. C.; Robertson, Katherine N.; Saberov, Vagiz Shamilievich; Glinyanaya, Nataliya V.; Rayenko, Gennady F.; Shvaika, O. P.

doi:10.24820/ark.5550190.p010.110

Cited by 14 publications

(4 citation statements)

References 249 publications

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“…Серед гетероциклічних конденсованих систем [21] найважливішими видаються похідні фенантро[9,10-d]імідазол-2-ілідену. На відміну від відомих аценафтенімідазол-2-іліденів (16-n-π) [22] вони є єдиною ароматичною 18-n-π-електронною системою.…”

Section: синтез конденсованих імідазол-2-іліденів та їх аналогівunclassified

Palladium carbene complexes – efficient catalysts for hydrodehalogenation of haloarenes

Коротких¹,

Saberov²,

Rayenko³

et al. 2021

New Functional Substances and Materials for Chemical Engineering

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The work is aimed at solving the problem of neutralization of persistent organic pollutants by catalytic methods. In order to identify the relationship between electronic and steric factors of carbenes with catalytic efficiency in the reaction of hydrodehalogenation of haloarenes, the parameters for estimating the ligand influences are proposed (electronic - Ie indices, Ph philicities, ED electron donicities, and EA electron acceptabilities, steric - dimerization energies) using theoretical methods (DFT, B3LYP5, RHF). Synthesis of new heteroaromatic carbenes of the series of sterically shielded 1,3-diarylphenanthro-[9,10-d]imidazol-2-ylidene, 1,3-diaryl-2-methylenephenanthro-[9,10-d]imidazoline, tetrahydropyrimidin-2-ylidene, 1,3-diarylimidazol-2-ylidene, 1,3,4-triaryl-1,2,4-triazol-5-ylidenes, their carbene complexes with palladium iodide, as well as the carbene complex of the superbasic anionic carbene 1,3-bis-(4-oxidophenyl)-imidazol-2-ylidene with nickel(II) ion. 1H and 13C NMR spectroscopy, mass spectrometry and X-ray diffraction study methods were used to establish the structures of the synthesized compounds. A high catalytic effect of a number of sterically shielded carbene complexes (2.4b, 3.5, 4.6a) in the reaction of hydrodehalogenation of p-dichlorobenzene haloarenes with sodium methoxide in isopropanol at 80 °С (TON 98000–110000) was revealed that can be applied to solve the problem of neutralization of persistent organic pollutants. The efficiency of catalysis by sterically open compounds 4.6b and 6.7 appeared to be low (TON 74, 128). The high catalytic effect of sterically shielded compounds is explained by the increased stability of the complexes under the conditions of an alkaline medium caused by metal alkoxides.

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Section: синтез конденсованих імідазол-2-іліденів та їх аналогівunclassified

Palladium carbene complexes – efficient catalysts for hydrodehalogenation of haloarenes

Коротких¹,

Saberov²,

Rayenko³

et al. 2021

New Functional Substances and Materials for Chemical Engineering

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show abstract

“…Several papers and reviews described the structure of the cations obtained by protonation of carbenes, alkylidene carbenes, and NHC . Carbene proton affinities calculated at G3MP2 level have also been reported (pp 75 and 95).…”

Section: Introductionmentioning

confidence: 99%

“…Solvation of NHCs by alcohols through HBs has been reported as well as the importance of HBs in the asymmetric catalysis with singlet NHCs .…”

Section: Introductionmentioning

confidence: 99%

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Interaction of N‐Heterocyclic Carbenes and Simple Carbenes with Small Molecules (One to Three Atoms) Excluding Metals: Formation of Covalent C–X Bonds

Alkorta

Elguero

2018

Journal of Heterocyclic Chem

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Synthesis and Biological Evaluation of a Library of AGE‐Related Amino Acid Triazole Crosslinkers

et al. 2020

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Three N‐Boc‐protected amino acids, l‐serine, l‐aspartic, and l‐glutamic acid, were either converted into their methyl azidoalkanoates or various alkynes via Bestmann‐Ohira strategy or via reaction with propargylamine and propargyl bromide, respectively. The Cu‐catalyzed click reaction provided a library of amino acid based triazoles, which were further N‐methylated to triazolium iodides or deprotected and precipitated as free amino acid triazole dihydrochlorides. The biological properties of all derivatives were investigated by cytotoxicity assay (against L929 mouse fibroblasts) and broth microdilution method (E. coli ΔTolC and S. aureus). First results reveal complete inactivity for triazolium iodides with cell viabilities and microbial growths nearly 100 %, indicating them as possible analogs of advanced glycation endproducts (AGEs).

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Synthesis and properties of heteroaromatic carbenes of the imidazole and triazole series and their fused analogues

Cited by 14 publications

References 249 publications

Palladium carbene complexes – efficient catalysts for hydrodehalogenation of haloarenes

Palladium carbene complexes – efficient catalysts for hydrodehalogenation of haloarenes

Interaction of N‐Heterocyclic Carbenes and Simple Carbenes with Small Molecules (One to Three Atoms) Excluding Metals: Formation of Covalent C–X Bonds

Synthesis and Biological Evaluation of a Library of AGE‐Related Amino Acid Triazole Crosslinkers

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