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, 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, Inorganic & Nuclear
Maria Makarova, Oleg I. Afanasyev, Fedor Kliuev, Yulia V. Nelyubina, Maria Godovikova, Denis Chusov
Summary: A systematic study was conducted on the influence of phosphine additives on the activity of a ruthenium catalyst in reductive amination without an external hydrogen source. It was found that nonhindered triarylphosphines with electron acceptor groups are the most effective activating agents, while trialkylphosphines strongly deactivate the ruthenium catalyst.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2021)
Review
Chemistry, Inorganic & Nuclear
C. T. Nandhu, Thaipparambil Aneeja, Gopinathan Anilkumar
Summary: This review summarizes the recent advances in rhodium-catalyzed reductive amination, where rhodium complexes are employed as catalysts with high efficiency and good selectivity.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Bin Cai, Han Wen Cheo, Tao Liu, Jie Wu
Summary: Carbon-based gas molecules are widely used feedstocks in industry, but face challenges in synthesizing fine chemicals. Recent research has focused on using these gaseous reagents in photoredox-promoted transformations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Maray Ortega, Raydel Manrique, Romel Jimenez, Miriam Parreno, Marcelo E. Domine, Luis E. Arteaga-Perez
Summary: The production of renewable chemicals from lignocellulosic biomass has gained attention in green chemistry, particularly the synthesis of secondary amines from phenolics using Pd/C and Rh/C catalysts. The study revealed a multi-step mechanism involving hydrogenation, condensation, and hydrogenation steps, with the order of reactions and activation energies determined.
Article
Chemistry, Multidisciplinary
Xinyu Wang, Yawen Jiang, Keke Mao, Wanbing Gong, Delong Duan, Jun Ma, Yuan Zhong, Jiawei Li, Hengjie Liu, Ran Long, Yujie Xiong
Summary: The study demonstrates that the interfacial CuAlO2 species efficiently stabilizes highly active sites on the Cu-CuAlO2-Al2O3 catalyst during harsh electrochemical conditions, leading to an ultradurable electrochemical CO2RR performance with high C2 selectivity.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Physical
Doaa R. Ramadan, Francesco Ferretti, Fabio Ragaini
Summary: This paper describes a palladium/phenanthroline catalyzed reductive cyclization of o-nitrobiphenyls to 9H-carbazoles operated by in situ released CO. The presence of phenyl formate is essential to avoid the use of high-pressure equipment and allows the reaction to be performed in a single thick-walled glass tube. The selectivity of the reaction is influenced by the identity of the base catalyzing the formate decomposition, and the stability of the catalyst is affected by the presence of chloride anions. The optimized catalytic system exhibits excellent stability and tolerance to moisture and air, enabling the reaction to be conducted with low catalyst loadings.
JOURNAL OF CATALYSIS
(2022)
Article
Chemistry, Physical
Dan Luo, Yurong He, Xin Yu, Fei Wang, Jiaojiao Zhao, Wentao Zheng, Haijun Jiao, Yong Yang, Yongwang Li, Xiaodong Wen
Summary: The type of active metal is the key factor determining the selectivity of primary amine, impacting the competitive hydrogenation reactions between primary imine and secondary imine.
JOURNAL OF CATALYSIS
(2021)
Article
Chemistry, Applied
Matthias Elfinger, Christof Bauer, Joerg Schmauch, Michael Moritz, Christoph Wichmann, Christian Papp, Rhett Kempe
Summary: This study presents an efficient method for the selective synthesis of differently substituted primary, secondary, and tertiary alkyl amines by combining borrowing hydrogen or hydrogen autotransfer and reductive amination with hydrogen. A nanostructured, bimetallic Co/Sc catalyst is used to mediate both reactions efficiently. The method shows broad product scope, good functional group tolerance, easy upscaling, and catalyst reusability.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Zhengyi Pan, Qian Zhang, Wenquan Wang, Lulin Wang, Guang-Hui Wang
Summary: In this study, a facile strategy was developed to synthesize two carbon-doped Ni catalysts, which can switch the selectivity in the reductive amination of biomass-derived carbonyl compounds and exhibit excellent stability and a broad substrate scope.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2022)
Article
Multidisciplinary Sciences
Tim Moeller, Michael Filippi, Sven Brueckner, Wen Ju, Peter Strasser
Summary: This study presents the design and analysis of a complete low-temperature, neutral-pH tandem CO2 electrolyzer cell chain. By coupling two different electrolyzer cells, the system achieves significantly enhanced production rates for C2+ chemicals and fuels directly from CO2 feeds. The results demonstrate the kinetic and practical energetic benefits of coupled tandem electrolyzer cell systems.
NATURE COMMUNICATIONS
(2023)
Article
Chemistry, Applied
Vincent Bernardin, Laurent Vanoye, Camila Rivera-Careamo, Philippe Serp, Alain Favre-Reguillon, Regis Philippe
Summary: Understanding the cooperative action of palladium nanoparticles (NPs) and palladium single atoms (SAs) supported on Ni is essential for developing more efficient supported transition metal catalysts. This work compared a series of Pd-catalysts on CNTs with the same palladium loading but different SA/NP ratios and demonstrated a synergy between the two palladium species (SAs and NPs). The study also identified the optimal distribution of surface palladium for maximum activity in the chosen test reactions.
Article
Chemistry, Organic
Lu Lei, Pei-Sen Zou, Zhi-Xin Wang, Cui Liang, Cheng Hou, Dong-Liang Mo
Summary: A regioselective Heck reaction catalyzed by a P-containing palladacycle was described, which affords 2-aryl-2,5-dihydrofurans and 2-aryl-2,3-dihydrofurans in good yields from 2,3-dihydrofuran with diaryliodonium salts and aryl iodides, respectively. Mechanistic studies and DFT calculations revealed the chemoselectivity and regioselectivity-determining step of this reaction.
Article
Chemistry, Organic
Wan-Jin Xiong, Lei Li, Jiang-Tao Li, Shi-Qiang Zhang, Jun-Lei Tang, Taigang Zhou
Summary: A catalyst-free chemoselective reductive amination using borane complex was developed for the synthesis of tertiary and secondary amines from primary amines and aldehydes. The reaction proceeds under mild conditions with good functional group compatibility and does not require any catalyst. Chemoselective control is achieved by manipulating the steric hindrance of the borane complex. This strategy was successfully applied to the synthesis of the anesthetic Tetracaine, and the potential mechanism was verified through isotope labeling experiments.
TETRAHEDRON LETTERS
(2023)
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)
