Article
Chemistry, Organic
Anuj Kumar, Muhammad Fahad Jamali, Shilpa Thomas, Shakir Ahamad, Ruchir Kant, Kishor Mohanan
Summary: An efficient additive-free cyclopropanation of 2-arylideneindane-1,3-dione has been achieved using trifluorodiazoethane, producing trifluoromethylated cyclopropanes with high yields and good functional group tolerance. The synthetic potential of this strategy is further demonstrated by the expedient synthesis of CF3-containing spiro-pyrrolines and organo-sulfur scaffolds, as well as providing an interesting substrate for regioselective Friedel-Crafts alkylation.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Babak Kaboudin, Samaneh Faghih, Sajedeh Alavi, Mohammad Reza Naimi-jamal, Alireza Fattahi
Summary: This study reports a solvent-free synthesis of 1-aminophosphonates via three-component or two-component reactions, and it is found that no solvent or catalyst is needed for the reactions. Furthermore, a novel method for the synthesis of N-deprotected 1-aminophosphonates is developed.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Organic
Jose M. Landeros, Carlos Cruz-Hernandez, Eusebio Juaristi
Summary: Organic-inorganic hybrid materials were prepared by intercalating amino acids and dipeptides into hydrotalcite through high speed ball milling and rehydration/reconstruction methods. The hybrid catalysts showed higher catalytic activities in the Michael addition reaction compared to pristine hydrotalcite-derived materials, providing high yields and enantioselectivity under neat reaction conditions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Victor Garcia-Vazquez, Pablo Martinez-Pardo, Alexandru Postole, A. Ken Inge, Belen Martin-Matute
Summary: This study developed a method for synthesizing chiral trifluoromethylated aliphatic amines, which involves organocatalytic isomerization and imine/enamine reduction to obtain compounds with two noncontiguous stereogenic centers in high yields and selectivities. The method is effective for primary amine substrates and provides a new pathway for synthesizing chiral trifluoromethylated scaffolds.
Article
Chemistry, Multidisciplinary
Tamara Dinhof, Thomas Kalina, Toda Stankovic, Kristof Braunsteiner, Philipp Rohrbach, Ertan Turhan, Andreas Gradwohl, Artur Koenigshofer, Jeannie Horak, Katharina Pallitsch
Summary: alpha-Aminophosphonic acids have a wide range of bioactivity and can serve as highly efficient transition state mimics. Although various methods for accessing enantiopure a-aminophosphonic acids have been reported, none of them can be applied universally for the synthesis of PaAAs. By using catalytic, stereoselective asymmetric transfer hydrogenation, phosphonic acid analogs of many alpha-amino acids can be obtained, which are important pharmaceutical building blocks and can be easily converted to a-aminophosphonic acids in most cases.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Maddalen Agirre, Tamara Bello, Jinxiu Zhou, Maria de Gracia Retamosa, Fernando P. Cossio
Summary: This study presents a method for the asymmetric synthesis of bicyclic highly substituted tetrahydropyrans, catalyzed by unnatural gamma-dipeptides based on densely substituted L-and D-proline derivatives. The one-pot reaction involves a ketone, a nitroalkene, and an aldehyde, resulting in an octahydro-2H-chromene scaffold. Monomeric species synthesized from which the y-dipeptides cannot catalyze the reaction, indicating the emergent nature of the catalytic behavior of these dimeric species.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Maddalen Agirre, Tamara Bello, Jinxiu Zhou, Maria de Gracia Retamosa, Fernando P. Cossio
Summary: The asymmetric synthesis of highly substituted tetrahydropyrans was achieved using unnatural gamma-dipeptides based on densely substituted L- and D- proline derivatives as catalysts. The dimeric species derived from these gamma-dipeptides showed emergent catalytic behavior in the one-pot reaction involving a ketone, a nitroalkene, and an aldehyde.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Yue Min, Jie Sheng, Jian-Liang Yu, Shan-Xiu Ni, Guobin Ma, Hegui Gong, Xi-Sheng Wang
Summary: A nickel-catalyzed asymmetric trifluoroalkylation of aryl iodides was described for the first time, demonstrating high efficiency, mild conditions, and excellent functional group tolerance, especially for substrates containing diverse pharmaceutical and bioactive molecules moieties. This strategy provided an efficient and facile way for diversity-oriented synthesis of chiral trifluoromethylated alkanes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Biochemistry & Molecular Biology
Aneta Kosinska, David Virieux, Jean-Luc Pirat, Kamila Czarnecka, Malgorzata Girek, Pawel Szymanski, Slawomir Wojtulewski, Saranya Vasudevan, Arkadiusz Chworos, Bogna Rudolf
Summary: The search for new inhibitors of biologically relevant targets is an important strategy in developing new drugs for the treatment of neurodegenerative diseases. A series of compounds were designed, synthesized, and evaluated for their inhibitory potential against acetylcholinesterase and butyrylcholinesterase. One of the compounds showed the strongest inhibition activity against acetylcholinesterase and cytotoxicity studies were also conducted.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Polymer Science
Oksana Velgosova, Livia Macak, Maksym Lisnichuk, Marek Vojtko
Summary: A chemical method was used to synthesize silver nanoparticles of various shapes. The shape of the nanoparticles affects the color of the colloid, and the ratio between precursor, reducing, and stabilizing agents is crucial for nanoparticle formation. The shape and size of AgNPs change over time, leading to a dichroic effect.
Article
Chemistry, Multidisciplinary
Adam Meares, Kimihiro Susumu, Divita Mathur, Sang Ho Lee, Olga A. Mass, Jeunghoon Lee, Ryan D. Pensack, Bernard Yurke, William B. Knowlton, Joseph S. Melinger, Igor L. Medintz
Summary: This study prepared a series of Cy5 derivatives with different 5,5'substituents for incorporation into DNA structures, and successfully incorporated them into nascent oligonucleotides. The photophysical properties of these DNA-labeled Cy5 derivatives exhibited similarities to the parent dyes, with either no change or an increase in fluorescence quantum yield depending on the sequence.
Article
Chemistry, Multidisciplinary
Nieves P. P. Ramirez, Jerome Waser
Summary: An asymmetric 3-component reaction catalyzed by a Cu-I-BOX catalyst was developed for the synthesis of chiral trifluoromethylated propargyl ethers and anilines. The reaction showed high enantioselectivity and yield with various nucleophiles and different electrophiles. The method also exhibited good diastereoselectivity with chiral substrates.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Floris Buttard, Pier Alexandre Champagne
Summary: In this study, the quinidinium-catalyzed phase-transfer cyanation reaction was investigated using density functional theory calculations. The 1,4-addition step was found to be the determining step for the selectivity of the reaction. Analysis of the binding modes between the catalyst and substrates revealed that the stabilization of the ammonium alpha-hydrogens is critical for the selectivity.
Article
Chemistry, Medicinal
Anna M. Rydzik, Doris Riether, Dirk Gottschling
Summary: This study reports the synthesis of 2'-fluoro and 2'-methoxy N6-methyladenosine phosphoramidites and their successful incorporation into oligonucleotides. The modifications of sugars in siRNAs with 2'-fluoro and 2'-methoxy are known to enhance stability, and N6-methylation modifies the potency of therapeutic silencing RNAs (siRNA). The combination of these modifications in the antisense strand of siRNA efficiently knocks down a target gene in cells. This work expands the pool of chemical modifications available for therapeutic siRNAs and provides tools for their efficient synthesis.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2023)
Article
Chemistry, Physical
Floris Buttard, Pier Alexandre Champagne
Summary: In this study, we conducted DFT calculations to investigate a specific phase-transfer catalyzed reaction, and found that the 1,4-addition step is the enantiodetermining step. The predicted results were in excellent agreement with the experimental results. Additionally, our analysis of the binding modes of the substrates with the catalyst revealed the key factors influencing the selectivity.
Article
Chemistry, Inorganic & Nuclear
O. M. Kozachkova, N. V. Tsaryk, V. I. Pekhnyo, V. V. Trachevskyi, A. B. Rozhenko, V. V. Dyakonenko
INORGANICA CHIMICA ACTA
(2018)
Article
Chemistry, Inorganic & Nuclear
Anatoliy Marchenko, Georgyi Koidan, Anastasiya Hurieva, Yurii Vlasenko, Alexander B. Rozhenko, Jean-Marc Sotiropoulos, Aleksandr Kostyuk
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2019)
Article
Chemistry, Organic
Evgeniy Y. Slobodyanyuk, Yulia L. Berezowska, Vitally V. Solomin, Dmitriy M. Volochnyuk, Alexander B. Rozhenko, Sergey Ryabukhin, Oleksandr O. Grygorenko
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Organic
Bohdan A. Chalyk, Kateryna V. Hrebeniuk, Yulia V. Fil, Konstantin S. Gavrilenko, Alexander B. Rozhenko, Bohdan V. Vashchenko, Oleksandr V. Borysov, Angelina V. Biitseva, Pavlo S. Lebed, Iulia Bakanovych, Yurii S. Moroz, Oleksandr O. Grygorenko
JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Multidisciplinary
Anatoliy Marchenko, Georgyi Koidan, Anastasiya Hurieva, Eduard Rusanov, Alexander B. Rozhenko, Aleksandr Kostyuk
HETEROATOM CHEMISTRY
(2020)
Article
Multidisciplinary Sciences
Rochelly da Silva Mesquita, Andrii Kyrylchuk, Iryna Grafova, Denys Kliukovskyi, Andriy Bezdudnyy, Alexander Rozhenko, Wanderli Pedro Tadei, Markku Leskela, Andriy Grafov
Article
Chemistry, Inorganic & Nuclear
O. M. Kozachkova, N. Tsaryk, O. O. Shtokvish, V. Pekhnyo, V. V. Trachevskii, A. B. Rozhenko, V. V. Dyakonenko
INORGANICA CHIMICA ACTA
(2020)
Article
Chemistry, Organic
Oleksandr A. Yesypenko, Anastasia O. Osipova, Oleksandr O. Tribrat, Sergii O. Kravchenko, Oleg M. Usachov, Viktoriya V. Dyakonenko, Aleksey B. Ryabitskii, Vladimir V. Pirozhenko, Svitlana Shishkina, Alexander B. Rozhenko, Vitaly Kalchenko
Summary: In this study, all three possible inherently chiral (cS)-propyloxy-octyloxy-calix[4]arene acetic acids were synthesized and their absolute configuration was determined. The complexation of these acetic acids with various chiral compounds was investigated using molecular modeling and H-1 NMR spectroscopy, revealing enantioselectivity in the binding of R- and S-forms of 2-aminobutanol.
Article
Chemistry, Organic
Anatoliy Marchenko, Georgyi Koidan, Anastasiya Hurieva, Kostiantyn Shvydenko, Alexander B. Rozhenko, Eduard B. Rusanov, Andrii A. Kyrylchuk, Aleksandr Kostyuk
Summary: Using DFT and ab initio calculations, it has been demonstrated that noncyclic formamidines can undergo thermal rearrangement into their isomeric aminocarbenes under rather mild conditions. The obtained silylformamidine has been shown to exhibit high reactivity as a nucleophilic carbene, reacting with various functional groups and displaying high mobility of the trimethylsilyl group. Similar behavior is predicted for some other silylated formamidines and related compounds based on calculation results.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Alexander B. Rozhenko, Yuliia S. Horbenko, Andrii A. Kyrylchuk, Evgenij V. Zarudnitskii, Sergiy S. Mykhaylychenko, Yuriy G. Shermolovich, Andriy V. Grafov
Summary: The unusual elongation of the C-S bond in sulfur-containing heterocycles can be explained by the formation of a donor-acceptor adduct of a carbene with an unsaturated ligand, with the stability of the system being crucial for further elongation. Carrying out isodesmic reactions of carbene exchange allows for quantification of the effect of carbene stability on the elongation of the C-S bond.
Article
Chemistry, Organic
Denys A. Kvasha, Andrii Deviatkin, Andrii S. Poturai, Pavel S. Nosik, Andrii A. Kyrylchuk, Sergiy Suikov, Alexander B. Rozhenko, Dmitriy M. Volochnyuk, Oleksandr O. Grygorenko
Summary: Imidazoles reacted with trimethyl(trifluoromethyl)silane-tetrabutylammonium difluorotriphenylsilicate (CF3SiMe3-TBAT) to undergo C-difluoromethylation at the C-2 position, with the intermediates 2-(trimethylsilyl)difluoromethyl-substituted derivatives eventually converting to 2-difluoromethyl-substituted imidazoles. Quantum chemical calculations propose two possible reaction mechanisms, both involving intermediate imidazolide anions stabilized by solvent molecules and counterions. These mechanisms proceed without high activation barriers.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Georgyi Koidan, Anastasiia N. Hurieva, Alexander B. Rozhenko, Uwe Manthe, Tobias Spengler, Serhii Zahorulko, Tetiana Shvydenko, Aleksandr Kostyuk
Summary: Silylformamidine 1 exists in equilibrium with itscarbenic form 1 ' due to an easy migration of thesilyl group. The reaction of 1 with variously substitutedfluorobenzenes proceeds as an insertion of the nucleophilic carbene 1 ' into the most acidic C-H bond upon mixingthe reagents and does not require any catalyst. The reaction provides aminals as the first products, whichcan easily be transformed into the corresponding aldehydes via acidichydrolysis. As silylformamidine 1 is tolerant to manyfunctional groups, the reaction can be applied to numerous benzenederivatives, making it a reliable strategy for application in organicsynthesis.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Inorganic & Nuclear
Yuriy Boiko, Konstantin Belikov, Ekaterina Bryleva, Zinaida Bunina, Victoria Varchenko, Alexander B. Rozhenko, Andriy Drapailo, Roman Rodik, Alexander Golub, Alexander Katz, Vitaly Kalchenko
Summary: This article describes a one-pot sequential reaction of silica gel with a tetrachlorosilane/triethylamine mixture and then with a conical upper rim tetraphosphorylated tetrahydroxy(thia)calixarenes, resulting in porous organo-inorganic sorbents modified by spatially ordered phosphonate, phosphinate, or phosphine oxide groups capable of cooperative binding of metal cations. The grafting process improves the efficacy of europium(III) sorption by the silica gels. DFT calculations reveal that the calixarene-Eu3+ complexes adopt a flattened cone conformation with coordination of the Eu3+ cation to three of the four P = O oxygen atoms and one of the aromatic systems, while the inclusion of three water molecules completely excludes cation-pi interactions.
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
(2023)
Article
Chemistry, Multidisciplinary
Petro P. Ony'sko, Tetyana Chudakova, Vladimir V. Pirozhenko, Alexandr B. Rozhenko
CURRENT GREEN CHEMISTRY
(2020)
Article
Mathematics, Applied
A. Rozhenko
NUMERICAL ANALYSIS AND APPLICATIONS
(2018)
Review
Chemistry, Multidisciplinary
Dan He, Yawen Li, Fuwen Zhao, Yuze Lin
Summary: High trap density in organic solar cells leads to localized charge carriers and reduced carrier lifetime, limiting device efficiency. This feature article summarizes the recent advances of trap suppression by material design and device engineering.
CHEMICAL COMMUNICATIONS
(2024)
Review
Chemistry, Multidisciplinary
Olivier Monfort, Arshitha Madhusudhan, Martin Motola
Summary: This article presents the advantages of coupling photocatalysis and Fenton-based processes for environmental remediation and discusses their synergy. It critically examines the simultaneous triggering of these two processes and provides insights into research approaches. The study aims to enhance understanding of this complex process and highlight the potential integration of new catalysts in current wastewater treatment technology.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Manideepa Dhar, Chittaranjan Mishra, Avijit Das, Uttam Manna
Summary: An approach of 'polymerization of monomers in its aggregated form' has been introduced to tailor the water wettability of fibrous and porous substrates, achieving hydrophobicity to superhydrophobicity transition, as well as patterned wettability. This facile chemical method provides a durable coating with adjustable and patterned wettability for various potential applications.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Saswat Ranjan Bhoi, Chhanda Debnath, Shikha Gandhi
Summary: In this article, a novel catalytic reaction using Pd(0) and Bronsted acid is reported for the synthesis of biologically important imidazolidinone-fused N-heterocycles through redox-neutral intramolecular N-allylation of indoles and pyrroles with alkynes. This atom-economical method is applicable to a wide range of substrates and eliminates the need for leaving groups or oxidizing agents commonly used in traditional allylation reactions.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Longkun Chen, Mingshuai Zhang, Meichen Liu, Zhuoyuan Liu, Yuetong Qiu, Zhilai Zhang, Fuchao Yu, Jiuzhong Huang
Summary: In this study, an efficient Rh(III)-catalyzed selective mono- and dual-C-H bond functionalization/cyclization with iodonium ylide as the sole coupling partner was demonstrated. Fused benzodiazepine skeletons were obtained in excellent yields, providing an improved approach to dual C-H unsymmetrical functionalization.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Alice Kennett, Sven Epple, Gabriella van der Valk, Irene Georgiou, Evelyne Gout, Romain R. Vives, Angela J. Russell
Summary: This study presents the design and synthesis of sulfated disaccharide inhibitors based on IdoA(2S)-GlcNS(6S), which showed potent inhibition of Sulf-2. The results suggest that IdoA(2S)-GlcNS(6S) is the shortest fragment size required for effective inhibition of Sulfs, and a trisulfated disaccharide is identified as the minimal fragment size of heparan sulfate for effective endosulfatase inhibition.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Mauro Garbini, Andrea Brunetti, Riccardo Pedrazzani, Magda Monari, Massimo Marcaccio, Giulio Bertuzzi, Marco Bandini
Summary: The self-adaptability of galvanostatic electrolysis was found to be helpful in a multistage chemo- and diastereoselective electrochemically promoted cyclodimerization of chalcones. Through a series of reductive events, densely functionalized cyclopentanes with five contiguous stereocenters were obtained (25 examples, yields up to 95%, dr values up to >20:1). Further experimental and electrochemical investigations indicated the crucial role of dynamic kinetic resolution of the aldol intermediate in the reaction mechanism.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Dhananjay S. Nipate, Neha Meena, Prakash N. Swami, Krishnan Rangan, Anil Kumar
Summary: In this study, the synthesis of functionalized benzo[a]phenazines and indazolo[2,3-a]quinolines was achieved through Rh(III)-catalyzed oxidative annulation of 2-arylquinoxalines and 2-aryl-2H-indazoles with allyl alcohols. The method showed a wide substrate scope, excellent functional group tolerance, good to high yields of annulated products, and the capability for scaled-up synthesis. A tentative mechanism of the annulation reaction was proposed based on a preliminary mechanistic investigation.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Ruonan Zhang, Abudukadi Tudi, Xia Yang, Xuping Wang, Zhihua Yang, Shujuan Han, Shilie Pan
Summary: A new lead tellurium borate material with a unique fundamental building block [B4O10] was synthesized and found to exhibit high birefringence. The structure-property relationship was discussed using first-principles calculations.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Amresh Kumar Singh, Baishali Thakurta, Anupam Giri, Monalisa Pal
Summary: This study introduces three key concepts for the quick synthesis of large-scale high-quality 2D materials films and their utilization in device fabrication.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Reina Hagiwara, Shun Nishimura, Kosuke Okeyoshi
Summary: A copolymer-conjugated nanocatalytic system has been developed to improve electron transfer and enhance photoinduced H2 generation.
CHEMICAL COMMUNICATIONS
(2024)
