Synthesis of heteroaromatic 3,3′-bridged biscarbenes of the 1,2,4-triazole series and their properties

Kiselyov, Artyom V.; Коротких, Н. И.; Cowley, Alan H.; Moore, Jennifer A.; Findlater, Michael; Pekhtereva, T. M.; Shvaika, O. P.

doi:10.3998/ark.5550190.0009.f29

Cited by 9 publications

(2 citation statements)

References 8 publications

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“…Firstly, 2-cyanmethyl derivative is obtained (1B); thereafter, having been heated in vacuum, it readily forms a stable carbene (1C). The second way is to deprotonate in the cold 1,2,4-triazole salts (2A) by sodium hydride in acetonitrile, which enables obtaining very pure derivatives of 1,2,4-triazole series (2B) [15], not only the monocarbenes, but also the biscarbenes, including those of conjugated type 2C, D (Scheme 2) [16][17][18]. Heating the carbenes (2B) with acetonitrile results in the formation of products of carbene inclusion into the C-H bond of acetonitrile [15].…”

Section: Inclusion Reactions and Synthesis Of Stable Carbenesmentioning

confidence: 99%

Chemistry of Stable Carbenes and «Green» Technologies

Коротких¹,

Саберов²,

Rayenko³

et al. 2015

Sci. innov.

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The fundamental researches in the chemistry of stable carbenes carried out by the L.M. Litvinenko Institute of Physical, Organic & Coal Chemistry of the NAS of Ukraine (IPOCC) over the last decade and applications in the field of «green» technologies based on the results of these researches have been described. Carbene versions of Claisen ester condensation with the formation of zwitterionic compounds, the Leuckart-Wallach reaction with the autoreduction of carbenoid azolium salts, the Hofmann cleavage of aminocarbene insertion products, induced tandem autotransformation of 1,2,4-triazol-5-ylidenes into 5-amidino-1,2,4-triazoles have been discovered. New carbene reactions of addition, deesterification, oxidation, and complex formation have been found. Effective methods for obtaining stable carbenes and carbenoids have been suggested. New types of carbenes, benzimidazolylidenes, superstable conjugated bis-carbenes, and carbenoids have been synthesized. The existence of hypernucleophilic carbenes has been theoretically predicted and experimentally confirmed. Prospects for the use of carbenes and their derivatives, in particular, carbene complexes of transition metals in the catalysis of organic reactions and the search of biologically active compounds have been outlined. K e y w o r d s: heteroaromatic carbenes, synthesis, properties, transformations, catalysis, biological activity, and «green» chemistry.

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Section: Inclusion Reactions and Synthesis Of Stable Carbenesmentioning

confidence: 99%

Chemistry of Stable Carbenes and «Green» Technologies

Коротких¹,

Саберов²,

Rayenko³

et al. 2015

Sci. innov.

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“…10 Biscarbenes with enhanced thermal and chemical stabilities featuring conjugated 3,3′-and 4,4′-bis-1,2,4-triazol-5-ylidenes have been synthesized and used as ligand supports for copper(I) complexes. 11,12 In a series of studies 1,2,4-triazol-5-ylidene complexes were prepared in situ from the corresponding salts (for the latest see, for example, ref. [13][14][15].…”

Section: Introductionmentioning

confidence: 99%

Syntheses of sterically shielded stable carbenes of the 1,2,4-triazole series and their corresponding palladium complexes: efficient catalysts for chloroarene hydrodechlorination

Glinyanaya¹,

Саберов²,

Коротких³

et al. 2014

Dalton Trans.

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The new sterically shielded 1,3,4-trisubstituted 1,2,4-triazol-5-ylidenes 8b-d were synthesized by a three step method starting from 2-phenyl-1,3,4-oxadiazole. The syntheses of palladium complexes 9a-d and 10a-d (including the sterically shielded derivatives 9c,d and 10a-d) were carried out via the reactions of the stable carbenes 8a-d with palladium halogenide salts in THF or toluene solution. Complexes 9c,dand 10a-d were found to be excellent catalysts for the reductive dechlorination (hydrodechlorination) of p-dichlorobenzene. The structures of 8c, 9a,b, and 10a were determined by single-crystal X-ray diffraction.

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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

et al. 2018

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The 1‐adamantyl substituted stable carbene 5 and the biscarbene 9 of the 1,2,4‐triazole series with sterically shielding groups at the position 4 of the heterocyclic ring (dbmp, dipp) have been synthesized in three steps starting from the derivatives of 1,3,4‐oxadiazole 1,6. A new method for the preparation of 1,3,4‐triaryl‐1,2,4‐triazol‐5‐ylidenes (14 a‐c) has also been proposed and includes the Vilsmeier reaction of 2‐benzoyl‐1‐formylphenylhydrazine with phosphorus chloroxide and aromatic amines, followed by deprotonation of the obtained 1,3,4‐triaryl‐1,2,4‐triazolium salts. The method allows introduction of steric shielding substituents to the 4‐position of the heterocycle. The resulting carbenes show promise as nucleophilic catalysts and ligands for carbene complex catalysts of organic reactions.

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Synthesis of heteroaromatic 3,3′-bridged biscarbenes of the 1,2,4-triazole series and their properties

Cited by 9 publications

References 8 publications

Chemistry of Stable Carbenes and «Green» Technologies

Chemistry of Stable Carbenes and «Green» Technologies

Syntheses of sterically shielded stable carbenes of the 1,2,4-triazole series and their corresponding palladium complexes: efficient catalysts for chloroarene hydrodechlorination

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

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