Sterically Shielded Stable Carbenes and Biscarbenes of the 1,2,4‐Triazole Series: A New Method for the Preparation of 1,3,4‐Triaryl‐1,2,4‐triazol‐5‐ylidenes

Glinyanaya, Nataliya V.; Коротких, Н. И.; Cowley, Alan H.; Williams, Owen M.; Jones, Richard A.; Lynch, Vincent M.; Kiselyov, Artyom V.; Rayenko, Gennady F.; Derevenets, Maria A.; Ryabitskii, Aleksey B.; Palomero, Orhi Esarte; Shvaika, O. P.

doi:10.1002/slct.201800658

Cited by 7 publications

(2 citation statements)

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“…Ароматичні похідні мають бути стабільними в лужному середовищі. Нами здійснено синтез невідомих 1,3,4-триарилзаміщених 1,2,4триазол-5-іліденів зі стерично екранованими замісниками в положенні 4 [31,32]. Для цього застосовано нову версію реакції Вільсмайєра дією на гідразид 5.2 хлороксиду фосфору та заміщених анілінів (рис.…”

Section: синтез стерично екранованих похідних 124-триазол-5-іліденівunclassified

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 стерично екранованих похідних 124-триазол-5-іліденівunclassified

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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“…Highly stable 1‐adamantyl‐3‐phenyl‐4‐(2,6‐dibenzhydrylphenyl)‐1,2,4‐triazol‐5‐ylidene was synthesized with good yield. The newly synthesized carbenes can be used as ligands for the preparation of new carbene complexes (Scheme ) …”

Section: Preparation Of 124‐triazole Derivativesmentioning

confidence: 99%

Exploring recent developments on 1,2,4‐triazole: Synthesis and biological applications

Sathyanarayana

Poojary

2020

J Chinese Chemical Soc

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Triazoles are nitrogen-bearing heterocycles. In the last few decades, researchers have focused on fused heterocycles, as they have better pharmacological effect compared to triazoles alone. Among the two isomers of triazole, this article aims to explore the work carried out on 1,2,4-triazole and N-bridged heterocycles derived from 1,2,4-triazole in last 18 years, highlight different synthetic pathways, and present a brief summary of the different biological activities possessed by 1,2,4-triazole derivatives. The information collected in this article is expected to help researchers to discover novel therapeutic agents for better applications in the field of pharmaceutical science. K E Y W O R D Sbio-organic chemistry, medicinal chemistry, organic chemistry

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Halogen-containing heteroaromatic carbenes of the 1,2,4-triazole series and their transformations

et al. 2021

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Sterically Shielded Stable Carbenes and Biscarbenes of the 1,2,4‐Triazole Series: A New Method for the Preparation of 1,3,4‐Triaryl‐1,2,4‐triazol‐5‐ylidenes

Cited by 7 publications

References 23 publications

Palladium carbene complexes – efficient catalysts for hydrodehalogenation of haloarenes

Palladium carbene complexes – efficient catalysts for hydrodehalogenation of haloarenes

Exploring recent developments on 1,2,4‐triazole: Synthesis and biological applications

Halogen-containing heteroaromatic carbenes of the 1,2,4-triazole series and their transformations

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