Review
Chemistry, Multidisciplinary
Craig E. Stival, Jason R. Zbieg, Peng Liu, Michael J. Krische
Summary: This article presents the research on the amination reaction catalyzed by pi-allyliridium-C,O-benzoate complexes. The experimental results show that this catalytic system can achieve highly stereoselective amination reactions and can be applied to various types of amines and nitronates. The study also reveals the mechanism of these reactions and the origin of the stereoselectivity.
ACCOUNTS OF CHEMICAL RESEARCH
(2022)
Article
Chemistry, Physical
Jian-Hua Liu, Qing Zhou, Yao Lin, Zhu-Lian Wu, Tian Cai, Wei Wen, Yan-Min Huang, Qi-Xiang Guo
Summary: In this study, a highly efficient atom-economic asymmetric alpha-allylation method using chiral-aldehyde/palladium catalyst was reported. This method enables the asymmetric alpha-allylation of different 1,3-dienes and allenes with N-unprotected amino acid esters, leading to the synthesis of alpha,alpha-disubstituted chiral alpha-amino acid esters with high efficiency, good yields, and stereoselectivities. No N-allylation byproducts were observed in these reactions. Two reaction models were proposed based on mechanistic control experiments. Overall, this work demonstrates a new approach for preparing structurally diverse chiral amino acids and provides insights for developing chiral-aldehyde catalytic systems.
Article
Biochemistry & Molecular Biology
Grzegorz Romanowski, Justyna Budka, Iwona Inkielewicz-Stepniak
Summary: New oxidovanadium(V) complexes and cis-dioxidomolybdenum(VI) complexes with chiral Schiff bases were characterized and studied for their catalytic, cytotoxic, and cytoprotective activities. The oxidovanadium(V) complexes showed higher cytotoxicity and no cytoprotective ability against H2O2-induced cytotoxicity.
Article
Chemistry, Physical
Aditi Bora, Subir Kr Maiti, Anmol Singh, Pranjit Barman
Summary: Three new chiral Schiff Bases (L-1, L-2, and L-3) were synthesized and characterized, with their crystal structures determined for L-1 and L-2. The study revealed the impact of remote substituents on both structure and biological activity of the Schiff bases, and investigated their interaction with calf-thymus DNA using various methods. The DNA binding affinity was found to be highest for L-3 among the three Schiff Bases.
JOURNAL OF MOLECULAR STRUCTURE
(2021)
Article
Chemistry, Multidisciplinary
Pratap Odedra, Atul Rojivadiya
Summary: The synthesis of novel metal complexes using different transition metals like Co, Cu, and Ni with a specific ligand was conducted. The molecular structure of the ligand was determined through various spectroscopic techniques, and thermal analyses of the synthesized metal complexes were carried out. Furthermore, the antimicrobial activity of these metal complexes was tested against selected bacterial and fungal strains, showing good to moderate biological activity in DMF and DMSO solvents.
INDIAN JOURNAL OF CHEMISTRY SECTION A-INORGANIC BIO-INORGANIC PHYSICAL THEORETICAL & ANALYTICAL CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
D. Yu Matuzko, L. M. Pevzner, M. L. Petrov, A. Ponyaev
Summary: Methods for synthesizing 4-(3-nitro-4-methoxyphenyl)-, 4-(2,5-dimethoxy-3-nitrophenyl)-, and 4-(2,5-dimethoxy-4-nitrophenyl)-1,2,3-thiadiazoles and reducing them to amines using zinc and acetic acid in isopropyl alcohol were developed. Luminescent compounds were then synthesized using the obtained amines and salicylic aldehyde Schiff bases.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY
(2021)
Article
Chemistry, Organic
I. Mineeva
Summary: The allylation of alpha-hydroxy Schiff bases with various 2-substituted functionalized allyl bromides under different allylating systems based on indium and zinc has been reported for the first time, resulting in the formation of a series of new alpha-amino alcohols with the generation of a new chiral center.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Artemy R. Fatkulin, Oleg I. Afanasyev, Alexey A. Tsygankov, Denis Chusov
Summary: This study demonstrates a significant increase in the catalytic activity of ruthenium catalysts in reductive amination after the addition of iodide to the reaction mixture. High turnover numbers and preparative yields of the products were achieved.
JOURNAL OF CATALYSIS
(2022)
Article
Chemistry, Physical
Evgeniya Podyacheva, Oleg Afanasyev, Vladimir S. Ostrovskii, Denis Chusov
Summary: This study demonstrates that the usage of syngas as a reducing agent can lead to more efficient and selective catalytic reduction reactions. Based on control experiments, a plausible mechanism for the superior performance of syngas is proposed. This approach is successfully applied to three reactions, achieving high catalyst turnover numbers and improved selectivity and functional group compatibility compared to hydrogen gas.
Review
Chemistry, Physical
Evgeniya Podyacheva, Oleg Afanasyev, Dmitry V. Vasilyev, Denis Chusov
Summary: Borrowing hydrogen or the hydrogen autotransfer amination is a powerful and atom-efficient method for creating single C-N bonds from stable and readily available substrates. This method is considered to be green and is highly efficient in synthesizing complex amines.
Article
Chemistry, Physical
Andrey S. Kozlov, Oleg I. Afanasyev, Denis Chusov
Summary: Borrowing hydrogen amination is a common method for the formation of C-N bonds, which can be carried out without transition metal catalysts at low temperatures. Through experimental investigation, optimal conditions can be predicted and the need for transition metal catalysts can be determined.
JOURNAL OF CATALYSIS
(2022)
Article
Chemistry, Organic
Oleg I. Afanasyev, Fedor S. Kliuev, Alexey A. Tsygankov, Yulia V. Nelyubina, Evgenii Gutsul, Valentin V. Novikov, Denis Chusov
Summary: This study demonstrates that the simple in situ addition of fluoride to asymmetric organometallic catalysts can improve both their activity and enantioselectivity. The approach has been successfully applied to prepare several enantioenriched GABA analogues.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Sofiya A. Runikhina, Alexey A. Tsygankov, Oleg I. Afanasyev, Denis Chusov
Summary: The addition of fluoride additive enables the use of milder conditions for the reductive alkylation of aldehydes with ketones using carbon monoxide as a reducing agent, using the readily available ruthenium catalyst [(p-cymene)RuCl2]. This method exhibits a broad substrate scope, and a probable explanation for the role of fluoride was provided.
MENDELEEV COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Andrey S. Kozlov, Oleg I. Afanasyev, Mikhail A. Losev, Maria I. Godovikova, Denis Chusov
Summary: A variety of amines and N-heterocycles were used as additives in the CO-assisted Ru-catalyzed reductive amination of p-anisaldehyde with p-anisidine. Pyridine showed strong activation for low active aliphatic substrates, while bidentate heterocyclic ligands significantly inhibited the catalyst for most substrates.
MENDELEEV COMMUNICATIONS
(2023)
Article
Chemistry, Physical
Denis Chusov, Gary A. A. Molander, Virginie Ratovelomanana-Vidal, Olivier Riant, Emmanuelle Schulz
Summary: In this paper, we discuss the extensive scholarly contributions of Professor Henri B. Kagan, our mentor and colleague, and the significant impact of his research on various fields of chemistry, including asymmetric oxidation, asymmetric reduction, unique features in lanthanide chemistry, issues of nonlinear effects, and the question of the origin of chirality on earth.
Article
Chemistry, Physical
Klim O. Biriukov, Svetlana A. Belova, Semyon Dudkin, Oleg I. Afanasyev, Maria Godovikova, Denis Chusov
Summary: This study demonstrates that fluoride additives can enhance the catalytic activity of metal complexes, even for complexes with 5- and 6-period metals. By using tetraphenylporphyrin and phthalocyanine hafnium complexes as examples, the catalyst loading was reduced to 500 ppm. It was observed that tetraphenylporphyrin complex decomposed after the reaction, while the phthalocyanine complex did not undergo such decomposition. In addition, hafnium tetrachloride showed high catalytic activity similar to both tetraphenylporphyrin and phthalocyanine complexes in the presence of fluoride additive.
MOLECULAR CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Evgeniya Podyacheva, Alexandra I. Balalaeva, Oleg I. Afanasyev, Sofiya A. Runikhina, Olga Chusova, Andrey S. Kozlov, Saihu Liao, Denis Chusov
Summary: Current approaches to reductive amination lack selectivity, require complex catalysts, or are not atom-economical. This study demonstrates the use of syngas as a mild and selective reducing agent for aminating carbonyl compounds with functional groups that are unstable under hydrogenation conditions. The method has a broad substrate scope and amino acid precursor and furfurylamine derivative were prepared, showing high selectivity. Several products with antifungal activity higher than triadimefon were synthesized.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Sofiya A. Runikhina, Oleg I. Afanasyev, Ekaterina A. Kuchuk, Dmitry S. Perekalin, Rajenahally V. Jagadeesh, Matthias Beller, Denis Chusov
Summary: Converter gas, a large scale waste product, is usually burned and contributes to greenhouse gas emissions. However, this study shows that it can be utilized as a reducing agent in organic reactions to produce valuable pharmaceuticals and agrochemicals. The gas was used in the synthesis of amide-based drug molecules and classical reductive amination reactions.
Article
Chemistry, Multidisciplinary
Artemy R. Fatkulin, Vasily Korochantsev, Oleg I. Afanasyev, Evgeniya Podyacheva, Olga Chusova, Dmitry V. Muratov, Maria I. Godovikova, Sergei Semenov, Denis Chusov
Summary: Here, we report a metal- and acid-free protocol for the reductive amination of carbonyl compounds using DMF and a substoichiometric amount of NaH2PO2·H2O. Various N,N-dimethylamines were obtained in moderate to excellent yields without the need for chromatographic purification. The method's trends and limitations with different formamides as sources of dialkyl fragments were explored.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Mikhail A. Losev, Andrey S. Kozlov, Vladimir B. Kharitonov, Oleg I. Afanasyev, Fedor S. Kliuev, Ludmila A. Bulygina, Natalya S. Khrushcheva, Dmitry A. Loginov, Denis Chusov
Summary: A simple and selective method using carbon monoxide as a reducing agent was developed for the preparation of amides from nitroarenes and carboxylic acids. The protocol does not require non-gaseous additives, simplifying product isolation and saving reducible functional groups.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Mikhail A. Losev, Andrey S. Kozlov, Vladimir B. Kharitonov, Oleg I. Afanasyev, Fedor S. Kliuev, Ludmila A. Bulygina, Natalya S. Khrushcheva, Dmitry A. Loginov, Denis Chusov
Summary: A straightforward and selective method using carbon monoxide as a reductant was developed to prepare amides directly from nitroarenes and carboxylic acids. This protocol simplifies product isolation by not requiring any non-gaseous additives and preserves reducible functional groups.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Evgeniya A. Trifonova, Nikita M. Ankudinov, Denis A. Chusov, Yulia Nelyubina, Dmitry S. Perekalin
Summary: This study successfully eliminates a common problematic step in the synthesis of chiral catalysts by using a specific ligand.
CHEMICAL COMMUNICATIONS
(2022)
