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Direct reductive amination of camphor using iron pentacarbonyl as stoichiometric reducing agent: features and limitations
European Journal of Organic Chemistry. 2020. Vol. 2020. No. 39. P. 6289-6294.
The method of direct reductive amination of camphor and fenchone was proposed. The most effective reducing agent is iron carbonyl. No ligands or solvents are needed. The stereochemistry of the corresponding products was determined by HMBC, HSQC, and NOESY spectra. The limitations of the method were shown. The reaction of camphor with primary amines led to exclusively exo product, while the reaction of fenchone led to exclusively endo product. The reaction of camphor with cyclic secondary amines led to the mixture of endo and exo isomers.
Artemy R. Fatkulin, Korochantsev V., Afanasyev O. et al., New Journal of Chemistry 2023 Vol. 47 P. 6532-6535
Herein we report a transition-metal- and acid-free protocol for the reductive amination of carbonyl compounds with DMF using a substoichiometric amount of NaH2PO2-H2O. A set of various N,Ndimethylamines were obtained in moderate to excellent yields without chromatographic purification. The general trends and limitations of the method with different formamides as sources of dialkyl-fragments were explored. ...
Added: October 25, 2023
Fatkulin A., Afanasyev O., Tsygankov A. et al., Journal of Catalysis 2022 Vol. 405 P. 404-409
Catalytic reductive reactions are essential for laboratory and industrial-scale organic synthesis. However, the nowadays trend is the development of new, progressively more complicated reducing systems, which hinders the application of such highly efficient approaches in practice. Another way to achieve highly active systems is enhancing the activity of the earlier developed catalysts with simple structures. ...
Added: January 11, 2022
Afanasyev O., Kuchuk E., Muratov K. et al., European Journal of Organic Chemistry 2021 Vol. 2021 No. 4 P. 543-586
Tertiary amines represent a key class of organic molecules with multiple industrial, synthetic, and analytical applications. The focus of this review is on different approaches towards the synthesis of the C3 and C3V symmetrical tertiary amines. Generally, symmetrical tertiary amines can be prepared via N‐alkylation with alkyl halides and alcohols, reductive amination, desamination, hydroamination of olefins, and ...
Added: March 29, 2021
Evgeniya Podyacheva, Balalaeva A., Afanasyev O. et al., New Journal of Chemistry 2023 Vol. 47 P. 10514-10518
Current approaches to the reductive amination are often non selective, require complicated catalysts or not atom-economical. Application of syngas as a mild and selective reducing agent to aminate carbonyl compounds with unstable under hygrogenation conditions functional groups furnishing the broad substrate scope is demonstrated herein. Amino acid precursor and furfurylamine derivative were prepared indicating the ...
Added: October 25, 2023
Afanasyev O., Kuchuk E., Usanov D. et al., Chemical Reviews 2019 Vol. 119 No. 23 P. 11857-11911
Reductive amination plays a paramount role in pharmaceutical and medicinal chemistry owing to its synthetic merits and the ubiquitous presence of amines among biologically active compounds. It is one of the key approaches to C–N bond construction due to its operational easiness and a wide toolbox of protocols. Recent studies show that at least a ...
Added: August 5, 2020
Phosphine ligands in the ruthenium-catalyzed reductive amination without an external hydrogen source
Makarova M., Afanasyev O., Kliuev F. et al., Journal of Organometallic Chemistry 2021 Vol. 941 Article 121806
A systematic study of the phosphine additives influence on the activity of a ruthenium catalyst in reductive amination without an external hydrogen source was carried out. [CymeneRuCl2]2 was used as a reference catalyst, and a broad set of phosphines including Alk3P, Alk2ArP, Ar3P and X3P was screened. Three complexes of general formula (Cymene)RuCl2PR3 were isolated in a ...
Added: April 13, 2021
Nikolaev S. A., Tsodikov M. V., A. V. Chistyakov et al., Catalysis Today 2021 Vol. 379 P. 50-61
PdCu/Al2O3 (Pd = 0.1 wt.%, Cu = 0.1 wt.%) catalyst and its monometallic analogues (Pd/Al2O3 and Cu/Al2O3) were prepared by combination of deposition-precipitation and impregnation methods. The structure of the catalysts was studied by means of XRD, TEM, EDS, TPD-NH3, and DRIFTS. In a standard run (275 ○C, 5 h), Cu/Al2O3 converts 11 % of ethanol to α-alcohols with ...
Added: November 11, 2023
Андрюшечкин Б. В., Eltsov K., Pavlova T. et al., Journal of Chemical Physics 2018 Vol. 148 No. 24 Article 244702
The adsorption of O-2 on Ag(111) between 300 and 500 K has been studied with temperature-programmed desorption (TPD) and scanning tunneling microscopy (STM). At the first stage of adsorption, the disordered local oxide phase (commonly looking in STM as an array of black spots) is formed on the surface irrespective of the substrate temperature. The maximum concentration of black spots was found to be approximate to 0.11 ML, which corresponds to an oxygen coverage of approximate to 0.66 ML. Taking into account that the nucleation of the Ag(111)-p(4 x 4)-O phase starts after the saturation of the disordered phase, one ...
Added: October 25, 2021
I. V. Sedov, Arutyunov V. S., Tsvetkov M. V. et al., Eurasian Chemico-Technological Journal 2022 Vol. 24 No. 2 P. 157-163
The possibility of using coalbed methane to produce methanol is assessed. Methanol can be obtained from methane both by direct partial oxidation and from synthesis gas formed through the oxidative conversion of methane. Thermodynamic analysis of coalbed methane conversion was carried out to determine the conditions for obtaining synthesis gas with the ratio [H2 ]/[CO] = ...
Added: October 7, 2022
Trifonova E., Ankudinov N., Mikhaylov A. A. et al., Angewandte Chemie - International Edition 2018 Vol. 57 No. 26 P. 7714-7718
The rapid development of enantioselective C−H activation reactions has created a demand for new types of catalysts. Herein, we report the synthesis of a novel planar‐chiral rhodium catalyst [(C5H2tBu2CH2tBu)RhI2]2 in two steps from commercially available [(cod)RhCl]2 and tert‐butylacetylene. Pure enantiomers of the catalyst were obtained through separation of its diastereomeric adducts with natural (S)‐proline. The catalyst promoted enantioselective ...
Added: September 29, 2020
Shirokova V., Ikonnikova V., Solyev P. et al., Synthesis 2021 Vol. 53 No. 24 P. 4689-4699
Directly accessible 8-substituted tetrahydroquinolines undergo 1,5-hydride shift-triggered cyclization to provide hardly accessible julolidine derivatives in 20-98% yield under scandium (III) triflate catalysis. The scope of the reaction, several follow-up transformations and a remarkable side-process discovered during the conditions optimization are highlighted. ...
Added: July 29, 2021
Svitanko I., Pivina T. S., Khakimov D. V., Journal of Molecular Modeling 2024 Vol. 30 Article 93
Using quantum chemistry and atom–atom potential methods, the molecular and crystal structures of cubane 1 and all types of unsubstituted azacubanes 2–22 were calculated. Alternative possible polymorphs of cubane 1 have been proposed. The thermochemical properties of azacubanes in the gas and solid phases were assessed. Thermodynamic aspects of stability are considered, and a significant ...
Added: March 13, 2024
Astakhov A., Chernenko A., Kutyrev V. et al., Inorganic Chemistry Frontiers 2023 Vol. 10 No. 1 P. 218-239
C-Amino-1,2,4-triazoles are challenging polynitrogen substrates for metal-catalyzed arylation due to their multidentate character, enhanced coordinating ability and decreased nucleophilicity of the amino group. In the present study, the Buchwald–Hartwig cross-coupling of diverse 3(5)-amino-1,2,4-triazoles with aryl chlorides and bromides delivering (hetero)arylamino-1,2,4-triazoles in good-to-excellent yields under Pd/NHC catalysis was developed. The use of Pd complexes with bulky ...
Added: February 14, 2024
Faraonov M., Romanenko N., Mikhailenko M. et al., New Journal of Chemistry 2021 Vol. 45 P. 13599-13607
Reduction of organic dye trans-perinone (its abbreviation is perinone) in different experimental conditions allows us to obtain and characterize radical anion {cryptand(K+)}[perinone˙−] (1) and dianion {PPN+}2[perinone2−]·2C6H4Cl2 (2) salts of this dye. The salts have layered structures. Perinone˙− radical anions form π–π stacked dimers in 1 with an effective interaction between them, whereas perinone2− dianions are ...
Added: October 21, 2022
Lototskyy M., Davids M. W., Sekgobela T. K. et al., Inorganics 2023 Vol. 11 No. 8 Article 319
Hydrolysis of light metals and hydrides can potentially be used for the generation of hydrogen on-board fuel cell vehicles, or, alternatively, for refilling their fuel tanks with H2 generated and pressurised without compressor on site, at near-ambient conditions. Implementation of this approach requires solution of several problems, including the possibility of controlling H2 release and ...
Added: August 11, 2023
Yurova P., Караванова Ю. А., Yaroslavtsev A. B., Журнал неорганической химии 2015 Т. 60 № 11 С. 1551-1553
The properties of hybrid materials based on the MK-40 heterogeneous membrane, the MF-4SK homogeneous membrane, and zirconium oxide with a functionalized surface are studied. The ionic conductivity and diffusion parameters of these materials were studied. The presence of the asymmetry effect of diffusion permeability and mutual diffusion of HCl and NaCl solutions through the studied ...
Added: November 13, 2019
Panina I., Balandin S., Tsarev A. et al., International Journal of Molecular Sciences 2023 Vol. 24 No. 2 P. 1
To date, a number of lantibiotics have been shown to use lipid II — a highly conserved peptidoglycan precursor in the cytoplasmic membrane of bacteria — as their molecular target. The α-component (Lchα) of the two-component lantibiotic lichenicidin (Lchα), previously isolated from the Bacillus licheniformis VK21 strain, seems to contain two putative lipid II binding ...
Added: February 21, 2023
Maslov V., Теоретическая и математическая физика 2019 Т. 201 № 1 С. 65-83
We study the process of a nucleon separating from an atomic nucleus from the mathematical standpoint
using experimental values of the binding energy for the nucleus of the given substance. A nucleon becomes
a boson at the instant of separating from a fermionic nucleus. We study the further transformations of
boson and fermion states of separation in a ...
Added: November 1, 2019
Victoria A. Vasileva,, Daria A. Mazur, Yury A. Budkov, Journal of Chemical Physics 2023 Vol. 159 No. 2 Article 024709
In this paper, we present a continuation of our research on modeling electrolyte solutions within charged pores. We make use of the model developed by Blossey et al. [Phys. Rev. E 95, 060602 (2017)], which takes into account the structural interactions between ions through a bilinear form over the gradients of local ionic concentrations in ...
Added: July 14, 2023
Wiley, 2022
Nitrogen-Rich Energetic Materials
Provides in-depth and comprehensive knowledge on both the chemistry and practical applications of nitrogen-rich energetic materials
Energetic materials, a class of material with high amounts of stored chemical energy, include explosives, pyrotechnics, and propellants. Initially used for military applications, nitrogen-rich energetic materials have become important in the civil engineering and aerospace sectors, they are ...
Added: January 31, 2023
Yurova P., Малахова В. Р., Gerasimova E. V. et al., Polymers 2021 Vol. 13 No. 15 P. 2513
Low chemical durability of proton exchange membranes is one the main factors limiting their lifetime in fuel cells. Ceria nanoparticles are the most common free radical scavengers. In this work, hybrid membranes based on Nafion-117 membrane and sulfonic or phosphoric acid functionalized ceria synthesized from various precursors were prepared by the in situ method for ...
Added: February 3, 2022
Budkov Y., Kolesnikov A. L., Polymer Science - Series C 2018 Vol. 60 No. Supplement 1 P. 148-159
Theoretical models of the conformational behavior of flexible polymer chains in mixed solvents enunciated in the world literature during the last decade are critically reviewed. Models describing different mechanisms of coil-to-globule transitions in a good solvent induced by cosolvent addition are highlighted. Special attention is given to the analysis of theoretical approaches to describing the ...
Added: November 30, 2018
Tatiana L. Kulova, Skundin A., Gavrilin I. M. et al., Batteries 2022 Vol. 8 No. 8 Article 98
Nanostructure composites Ge-Co-P with brutto-composition CoGe2P0.1, or CoGe2@GeP were manufactured via electrolysis of aqueous electrolyte. Such composites are able to reversible insertion of lithium and sodium with specific capacities up to 855 and 425 mAh/g, respectively. The main advantage of the composites consists in their excellent cycleability. ...
Added: November 25, 2022
Medvedev M., Belyy A., Levina A. et al., European Journal of Organic Chemistry 2019 Vol. 2019 No. 26 P. 4133-4138
The reaction of di(methoxycarbonyl)tetrazine with substituted cycloprop-2-ene-1-carboxylates gives a series of 3,4-diazanorcaradienes and 1,2-diazepines. The influence of the nature of cyclopropenes and the reaction conditions on its selectivity was investigated. The addition of nucleophiles to norcaradienes was studied and a rare example of the “walk” rearrangement in this class of compounds was revealed. ...
Added: October 12, 2019