1‐(Furan‐2‐ylmethyl)‐1<i>H</i>‐tetrazole and its Copper(II) Complexes

Andreeva, T. N.; Lyakhov, Alexander S.; Ivashkevich, Ludmila S.; Войтехович, Сергей В.; Grigoriev, Yuri V.; Ивашкевич, Олег А.

doi:10.1002/zaac.201500550

Cited by 8 publications

(5 citation statements)

References 38 publications

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“…As for metal-involving bonds, the Cu(1)−Br(2) length of the terminal bromide ion (see Table 3 ) is about 0.06 Å shorter than the Cu(1)−Br(1) distance (2.3687 (6) vs. 2.4302 (4) Å); the Cu(1)−Br(1) I bond length of the µ-bridging Br ion is instead appreciably longer at 2.7600 (5), about 0.33 Å longer than the terminal Cu−Br bond. This value is higher than the reported average for similar compounds (2.59 Å) but fits within the reported range (2.37–3.06 Å) [ 82 , 83 , 84 , 85 , 86 , 87 , 88 ]. Similar considerations can apply to the Cu−N(1) and Cu−N(3) distances: respectively, 2.017 (2) and 2.042 (3) Å (mean: 2.00, range: 1.97–2.09 Å).…”

Section: Resultssupporting

confidence: 88%

“…The crystal structure investigation revealed that, in the solid state, the compound exists as a dimer of formula [Cu(L OHex )Br(μ-Br)] 2 , with the Br(1) ions binding two symmetry-related units to each other. To the best of our knowledge, this complex is one of the few mono- or di-nuclear bis-pyrazolyl acetate copper complexes [ 81 , 82 ] with uncoordinated acetate moieties, and also one of the relatively not-so-abundant copper complexes showing µ-bridging bromide ions coupled with two pentacyclic N-based ligands [ 83 , 84 , 85 , 86 , 87 , 88 ], described in the CCDC repository [ 89 ].…”

Section: Resultsmentioning

confidence: 99%

“…The aliphatic chain is placed in such a way as to fold towards the N(1):C(3) ring, with C(12)/C(12A) approximately 4 Å apart from the ring centroid. The Cu atom is penta-coordinated and the environment has a distorted square planar shape; this seems to be the preferred shape in similar compounds [ 82 , 83 , 84 , 85 , 86 , 87 , 88 ]. Sitting in the pyramid basal plane are the N(1) and N(3) atoms of the two pyrazolyl rings, which are in trans position with the Br(1) and Br(2) atoms, respectively.…”

Section: Resultsmentioning

confidence: 99%

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A New Dimeric Copper(II) Complex of Hexyl Bis(pyrazolyl)acetate Ligand as an Efficient Catalyst for Allylic Oxidations

et al. 2021

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A new dimeric copper(II) bromide complex, [Cu(LOHex)Br(μ-Br)]2 (1), was prepared by a reaction of CuBr2 with the hexyl bis(pyrazol-1-yl)acetate ligand (LOHex) in acetonitrile solution and fully characterized in the solid state and in solution. The crystal structure of 1 was also determined: the complex is interlinked by two bridging bromide ligands and possesses terminal bromide ligands on each copper atom. The two pyrazolyl ligands in 1 coordinate with the nitrogen atoms to complete the Cu coordination sphere, resulting in a five-coordinated geometry—away from idealized trigonal bipyramidal and square pyramidal geometries—which can better be described as distorted square pyramidal, as measured by the τ and χ structural parameters. The pendant hexyloxy chain is disordered over two arrangements, with final site occupancies refined to 0.705 and 0.295. The newly synthesized complex was evaluated as a catalyst in copper-catalyzed C–H oxidation for allylic functionalization through a Kharasch–Sosnovsky reaction without any external reducing agent. Using 0.5 mol% of this catalyst, and tert-butyl peroxybenzoate (Luperox) as an oxidant, allylic benzoates were obtained with up to 90% yield. The general reaction time was only slightly decreased to 24 h but a very significant decrease in the alkene:Luperox ratio to 3:1 was achieved. These factors show relevant improvements with respect to classical Kharasch–Sosnovsky reactions in terms of rate and amount of reagents. The present study highlights the potential of copper(II) complexes containing functionalized bis(pyrazol-1-yl)acetate ligands as efficient catalysts for allylic oxidations.

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Section: Resultssupporting

confidence: 88%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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A New Dimeric Copper(II) Complex of Hexyl Bis(pyrazolyl)acetate Ligand as an Efficient Catalyst for Allylic Oxidations

et al. 2021

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“…In the case of furcate substituents R ( tert ‐butyl, phenyl, 2,4,6‐trimethylphenyl), complexes of the composition Cu X 2 L 2 show 1D coordination motif of type B . Moreover, 1‐(furan‐2‐ylmethyl)tetrazole was also reported to generate dinuclear complexes Cu 2 X 4 L 4 of type C . In complexes of types A – C , tetrazoles show N 4 monodentate coordination (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

Copper(II) Halide Complexes with 1‐tert‐Butyl‐1H‐1,2,4‐triazole and 1‐tert‐Butyl‐1H‐tetrazole

Войтехович

Degtyarik

Lyakhov

et al. 2017

Zeitschrift anorg allge chemie

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1-tert-Butyl-1H-1,2,4-triazole (tbtr) was found to react with copper(II) chloride or bromide to give the complexes [Cu(tbtr) 2 X 2 ] n and [Cu(tbtr) 4 X 2 ] (X = Cl, Br). 1-tert-Butyl-1H-tetrazole (tbtt) reacts with copper(II) bromide resulting in the formation of the complex [Cu 3 (tbtt) 6 Br 6 ]. The obtained crystalline complexes as well as free ligand tbtr were characterized by elemental analysis, IR spectroscopy, thermal and X-ray analyses. For free ligand tbtr, 1 H NMR and 13 C NMR spectra were also recorded. In all the complexes, tbtr and tbtt act as monodentate ligands coordinated by Cu II cations via the * Dr. S. V. Voitekhovich Fax: +375172264696 E-Mail: azole@tut.by [a] 100 heteroring N 4 atoms. The triazole complexes [Cu(tbtr) 2 Cl 2 ] n and [Cu(tbtr) 2 Br 2 ] n are isotypic, being 1D coordination polymers, formed at the expense of single halide bridges between neighboring copper(II) cations. The isotypic complexes [Cu(tbtr) 4 Cl 2 ] and [Cu(tbtr) 4 Br 2 ] reveal mononuclear centrosymmetric structure, with octahedral coordination of Cu II cations. The tetrazole compound [Cu 3 (tbtt) 6 Br 6 ] is a linear trinuclear complex, in which neighboring copper(II) cations are linked by single bromide bridges. Scheme 1. 1-R-Tetrazoles and structural motifs of their copper(II) halide complexes.dentate coordination (Scheme 2). It should be noted that complexes of type A are of interest since they undergo ferromagnetic transition at temperatures lower than 10 K. [10] Scheme 2. The N 4 coordination mode of 1-R-tetrazoles and 1-R-1,2,4triazoles, realized in their copper(II) halide complexes.

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“…In continuation of our earlier synthetic and structural investigations of Cu II complexes with tetrazole ligands, [23][24][25][26] in the present work we aimed to design a ligand containing a tetrazolyl moiety that was capable of direct metallation with a copper salt. 1-(5-Amino-3-azapentyl)tetrazole, which has two amino groups that are potentially capable of achieving chelating coordination near the endocyclic carbon atom, was chosen for this purpose.…”

Section: Introductionmentioning

confidence: 99%

The first organocopper tetrazole derivative: synthesis and characterization

et al. 2016

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1-(5-Amino-3-azapentyl)tetrazole dihydrochloride (HL·2HCl) was prepared by heterocyclization of diethylenetriamine with triethyl orthoformate and sodium azide followed by treatment with potassium carbonate and hydrochloric acid. The reaction of CuCl2, HL·2HCl and triethylamine (NEt3) in a molar ratio of 1 : 1 : 3 in water was found to generate a novel organometallic tetrazole derivative Cu2L2Cl2. This compound is present as a binuclear centrosymmetric molecular complex, in which C-deprotonated tetrazole L acts as a chelating ligand via the two amino N and tetrazole ring C coordination sites and the two copper atoms are linked together through two tetrazole ring N(4)-C(5) bridges. This complex is the first organocopper tetrazole derivative. When the molar ratio of the reagents in the abovementioned reaction was changed to 1 : 2 : 2, the complex Cu(HL)2Cl2 was formed along with Cu2L2Cl2. Pure Cu(HL)2Cl2 was isolated after reaction of the reagents in a molar ratio of 1 : 3 : 6. The complex Cu(HL)2Cl2 is present as a mononuclear molecular complex, with a chelating coordination mode of HL via the two amino N atoms only. Both complexes as well as HL·2HCl were characterized by single-crystal X-ray analysis.

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1‐(Furan‐2‐ylmethyl)‐1H‐tetrazole and its Copper(II) Complexes

Cited by 8 publications

References 38 publications

A New Dimeric Copper(II) Complex of Hexyl Bis(pyrazolyl)acetate Ligand as an Efficient Catalyst for Allylic Oxidations

A New Dimeric Copper(II) Complex of Hexyl Bis(pyrazolyl)acetate Ligand as an Efficient Catalyst for Allylic Oxidations

Copper(II) Halide Complexes with 1‐tert‐Butyl‐1H‐1,2,4‐triazole and 1‐tert‐Butyl‐1H‐tetrazole

The first organocopper tetrazole derivative: synthesis and characterization

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