Heterocyclic carbene complexes of nickel, palladium, and copper(I) as effective catalysts for the reduction of ketones*

Коротких, Н. И.; Саберов, В. Ш.; Киселев, А. В.; Glinyanaya, Nataliya V.; Marichev, K. A.; Pekhtereva, T. M.; Dudarenko, Galina; Бумагин, Н. А.; Shvaika, O. P.

doi:10.1007/s10593-012-0947-9

Cited by 15 publications

(10 citation statements)

References 31 publications

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“…The subsequent reactions of the foregoing carbenes with palladium(II) chloride or palladium(II) iodide were carried out using a 1 : 1 molar ratio in THF solution at room temperature according to the literature procedure. 12 The outcomes of these reactions were found to be dependent on the steric demands of the nitrogen substituents. On the one hand, the reaction of the more bulky dbep substituted carbene 9a with palladium halogenides afforded the mononuclear carbene complexes 11a,b.…”

Section: Resultsmentioning

confidence: 99%

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Exceptionally efficient catalytic hydrodechlorination of persistent organic pollutants: application of new sterically shielded palladium carbene complexes

Саберов¹,

Evans

Коротких³

et al. 2014

Dalton Trans.

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A new sterically shielded carbene with branched aromatic substituents (9a) and two palladium halogenide complexes (11a,b) have been prepared. The single crystal X-ray structures of free carbene 9a and palladium carbene complexes 10b and 11a were determined. Very high catalytic efficiencies were evident for the sterically shielded palladium carbene complexes 10b and 11a,b when the latter complexes were employed as catalysts for hydrodechlorination of the chloroarenes p-dichlorobenzene and hexachlorobenzene. When optimized, the foregoing approach is significantly more effective than those of currently known transition metal carbene complexes. The most active catalysts were found to be the monocarbene complexes of palladium chloride and iodide, both of which feature highly branched aromatic substituents (11a,b).

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Section: Resultsmentioning

confidence: 99%

“…On the other hand, treatment of the less bulky dipp-substituted carbene 9b with PdI 2 resulted in the formation of the diiodo-bridged dinuclear palladium carbene complex 10b, and is reminiscent of the corresponding reaction with PdCl 2 . 12 …”

Section: Resultsmentioning

confidence: 99%

Exceptionally efficient catalytic hydrodechlorination of persistent organic pollutants: application of new sterically shielded palladium carbene complexes

Саберов¹,

Evans

Коротких³

et al. 2014

Dalton Trans.

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“…The desired copper complex 1c was produced by the reaction of equivalent CuCl with 1b under basic condition (Figs. S5 and S6 in the ESM) [38]. The cluster was prepared in one-pot (see Experimental Section in the ESM for more details).…”

Section: Synthesis and Characterizations Of Clusters Cu31h6 And Cu31d6mentioning

confidence: 99%

Copper-hydride nanoclusters with enhanced stability by N-heterocyclic carbenes

et al. 2021

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Copper-hydrides have been intensively studied for a long time due to their utilization in a variety of technologically important chemical transformations. Nevertheless, poor stability of the species severely hinders its isolation, storage and operation, which is worse for nano-sized ones. We report here an unprecedented strategy to access to ultrastable copper-hydride nanoclusters (NCs), namely, using bidentate N-heterocyclic carbenes as stabilizing ligands in addition to thiolates. In this work, a simple synthetic protocol was developed to synthesize the first large copper-hydride nanoclusters (NCs) stabilized by N-heterocyclic carbenes (NHCs). The NC, with the formula of Cu31(RS)25(NHC)3H6 (NHC = 1,4-bis(1-benzyl-1H-benzimidazol-1-ium-3-yl) butane, RS = 4-fluorothiophenol), was fully characterized by high resolution Fourier transform ion cyclotron resonance mass spectrum, nuclear magnetic resonance, ultra-violet visible spectroscopy, density functional theory (DFT) calculations and single-crystal X-ray crystallography. Structurally, the title cluster exhibits unprecedented Cu4 tetrahedron-based vertex-sharing (TBVS) superstructure (fusion of six Cu4 tetrahedra). Moreover, the ultrahigh thermal stability renders the cluster a model system to highlight the power of NHCs (even other carbenes) in controlling geometrical, electronic and surface structure of polyhydrido copper clusters.

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“…The consequence of these weakened bonds is evident not only in the above-mentioned decomposition of cyanomethylazolines to carbenes but also in the carbenoid properties of the cyanomethylazoline 79A, the reactions of which were carried out under the influence of metal salts to give the carbene complexes 79B,C (Scheme 79). 216,334,335 Scheme 79. Carbenoid reactions of 2-cyanomethyl-2H-benzimidazoline with copper(I) salts.…”

Section: Scheme 78 Carbenoid Decomposition Of Azolium Formatsmentioning

confidence: 99%

“…334 The chelated carbene complex of nickel 115A1 (R = 1-Ad, M = Ni) has shown high catalytic efficiency (TON 4500, TOF to 1500 h -1 ). However, the value for its palladium analogue 115A2 is significantly higher (TON 7000, TOF of 3500 h The high catalytic effect for the carbene complexes of copper(I) 115B,C could be due, at least in part, to a high degree of Cu-I ionization, which in turn could facilitate the exchange of halogen with the isopropoxide ion providing a reducing effect.…”

Section: Reduction Of Multiple Bonds With Alcohols (Hydrogen Transfer)mentioning

confidence: 99%

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

Коротких¹,

Cowley²,

Clyburne³

et al. 2017

Arkivoc

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Heterocyclic carbene complexes of nickel, palladium, and copper(I) as effective catalysts for the reduction of ketones*

Cited by 15 publications

References 31 publications

Exceptionally efficient catalytic hydrodechlorination of persistent organic pollutants: application of new sterically shielded palladium carbene complexes

Exceptionally efficient catalytic hydrodechlorination of persistent organic pollutants: application of new sterically shielded palladium carbene complexes

Copper-hydride nanoclusters with enhanced stability by N-heterocyclic carbenes

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

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