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1.	Shatskiy, Andrey, et al. (författare) Electrochemically Driven Water Oxidation by a Highly Active Ruthenium-Based Catalyst 2019 Ingår i: ChemSusChem. - : Wiley. - 1864-5631 .- 1864-564X. ; 12:10, s. 2251-2262 Tidskriftsartikel (refereegranskat)abstract The highly active ruthenium-based water oxidation catalyst [Ru-X(mcbp)(OHn)(py)(2)] [mcbp(2-)=2,6-bis(1-methyl-4-(carboxylate)benzimidazol-2-yl)pyridine; n=2, 1, and 0 for X=II, III, and IV, respectively], can be generated in a mixture of Ru-III and Ru-IV states from either [Ru-II(mcbp)(py)(2)] or [Ru-III(Hmcbp)(py)(2)](2+) precursors. The precursor complexes are isolated and characterized by single-crystal X-ray analysis, NMR, UV/Vis, EPR, and FTIR spectroscopy, ESI-HRMS, and elemental analysis, and their redox properties are studied in detail by electrochemical and spectroscopic methods. Unlike the parent catalyst [Ru(tda) (py)(2)] (tda(2-)=[2,2:6,2-terpyridine]-6,6-dicarboxylate), for which full transformation into the catalytically active species [Ru-IV(tda)(O)(py)(2)] could not be carried out, stoichiometric generation of the catalytically active Ru-aqua complex [Ru-X(mcbp)(OHn)(py)(2)] from the Ru-II precursor was achieved under mild conditions (pH7.0) and short reaction times. The redox properties of the catalyst were studied and its activity for electrocatalytic water oxidation was evaluated, reaching a maximum turnover frequency (TOFmax) of around 40000s(-1) at pH9.0 (from foot-of-the-wave analysis), which is comparable to the activity of the state-of-the-art catalyst [Ru-IV(tda)(O)(py)(2)].
2.	Abdel-Magied, Ahmed F., et al. (författare) Chemical and Photochemical Water Oxidation Mediated by an Efficient Single-Site Ruthenium Catalyst 2016 Ingår i: ChemSusChem. - : Wiley. - 1864-5631 .- 1864-564X. ; 9:24, s. 3448-3456 Tidskriftsartikel (refereegranskat)abstract Water oxidation is a fundamental step in artificial photosynthesis for solar fuels production. In this study, we report a single-site Ru-based water oxidation catalyst, housing a dicarboxylate-benzimidazole ligand, that mediates both chemical and light-driven oxidation of water efficiently under neutral conditions. The importance of the incorporation of the negatively charged ligand framework is manifested in the low redox potentials of the developed complex, which allows water oxidation to be driven by the mild one-electron oxidant [Ru(bpy)(3)](3+) (bpy = 2,2'-bipyridine). Furthermore, combined experimental and DFT studies provide insight into the mechanistic details of the catalytic cycle.
3.	Abdel-Magied, Ahmed F., et al. (författare) Substituent Effects in Molecular Ruthenium Water Oxidation Catalysts Based on Amide Ligands 2017 Ingår i: ChemCatChem. - : Wiley. - 1867-3880 .- 1867-3899. ; 9:9, s. 1583-1587 Tidskriftsartikel (refereegranskat)abstract The production of clean and sustainable energy is considered as one of the most urgent issues for our society. Mastering the oxidation of water to dioxygen is essential for the production of solar fuels. A study of the influence of the substituents on the catalytic activity of a series of mononuclear Ru complexes (2a-e) based on a tetradentate ligand framework is presented. At neutral pH, using [Ru(bpy)(3)](PF6)(3) (bpy=2,2'-bipyridine) as the terminal oxidant, a good correlation between the turnover frequency (TOF) and the Hammett sigma(meta) parameters was obtained. Additionally, a general pathway for the deactivation of Ru-based catalysts 2a-e during the catalytic oxidation of water through poisoning by carbon monoxide was demonstrated. These results highlight the importance of ligand design for fine-tuning the catalytic activity of water oxidation catalysts.
4.	Avetyan, David L., et al. (författare) Scalable total synthesis of natural vanillin-derived glucoside omega-esters 2022 Ingår i: Carbohydrate Research. - : Elsevier BV. - 0008-6215 .- 1873-426X. ; 522, s. 108683- Tidskriftsartikel (refereegranskat)abstract The first total synthesis of vanilloloside, calleryanin, and a series of naturally occurring omega-esters of vanilloloside was realized through direct glycosylation of vanillin-based aglycones or late-stage derivatization of vanilloloside. All aglycones and their fragments were synthesized from vanillin as the sole aromatic precursor. Subsequently, these intermediates were used to construct various vanillin-derived glucoside omega-esters using a mild acidic deacetylation as the key synthetic step, providing the final products in the total yields of 10-50% and general purity of >95%. Additionally, the first operationally simple and sustainable synthesis of litseafoloside B was realized on large scale, avoiding the use of toxic solvents and reagents, providing an attractive alternative to isolation of this and other similar compounds from plant sources.
5.	Chen, X., et al. (författare) Synthesis of Sulfonylated Heterocycles via Copper-Catalyzed Heteroaromatization/Sulfonyl Transfer of Propargylic Alcohols 2021 Ingår i: Chemistry - An Asian Journal. - : Wiley. - 1861-4728 .- 1861-471X. ; 16:1, s. 30-33 Tidskriftsartikel (refereegranskat)abstract An unprecedented copper-catalyzed heteroaromatization/sulfonyl transfer of propargylic alcohols with isocyanide has been developed. 3-Sulfonyl benzofurans and indoles were produced under Cu(I) catalysis in good to high yields. The developed catalytic methodology provides controlled, modular, and facile access to sulfonyl benzoheterocycle scaffolds.
6.	Chen, Y., et al. (författare) Cooperative Silver- and Base-Catalyzed Diastereoselective Cycloaddition of Nitrones with Methylene Isocyanides : Access to 2-Imidazolinones 2020 Ingår i: European Journal of Organic Chemistry. - : Wiley-VCH Verlag. - 1434-193X .- 1099-0690. Tidskriftsartikel (refereegranskat)abstract A protocol involving cooperative silver- and base-catalyzed diastereoselective cycloaddition of nitrones with isocyanides is described, providing access to a wide range of 2-imidazolinone derivatives with various functional groups as single diastereomers. Varying the base and temperature of the reaction allowed selective access to both diastereomers of the product. A plausible reaction mechanism is proposed and supported by DFT calculations.
7.	Chen, Yan, et al. (författare) Silver-Promoted (4+1) Annulation of Isocyanoacetates with Alkylpyridinium Salts : Divergent Regioselective Synthesis of 1,2-Disubstituted Indolizines 2021 Ingår i: Organic Letters. - : American Chemical Society (ACS). - 1523-7060 .- 1523-7052. ; 23:19, s. 7555-7560 Tidskriftsartikel (refereegranskat)abstract An unprecedented silver-promoted regioselective (4 + 1) annulation of isocyanoacetates with pyridinium salts is reported. The established protocol provides controlled, facile, and modular access to a range of synthetically useful N-fused heterocyclic scaffolds containing indolizines, pyrrolo[1,2-a]quinolines, pyrrolo[2,1-a]isoquinolines, and 1H-imidazo[4,5-a]indolizin-2(3H)-ones. A mechanistic pathway involving nucleophilic addition/protonation/elimination/cydoisomerization is proposed.
8.	Das, Biswanath, et al. (författare) The Impact of Ligand Carboxylates on Electrocatalyzed Water Oxidation 2021 Ingår i: Accounts of Chemical Research. - : American Chemical Society (ACS). - 0001-4842 .- 1520-4898. ; 54:17, s. 3326-3337 Forskningsöversikt (refereegranskat)abstract Fossil fuel shortage and severe climate changes due to global warming have prompted extensive research on carbon-neutral and renewable energy resources. Hydrogen gas (H-2), a clean and high energy density fuel, has emerged as a potential solution for both fulfilling energy demands and diminishing the emission of greenhouse gases. Currently, water oxidation (WO) constitutes the bottleneck in the overall process of producing H-2 from water. As a result, the design of efficient catalysts for WO has become an intensively pursued area of research in recent years. Among all the molecular catalysts reported to date, ruthenium-based catalysts have attracted particular attention due to their robust nature and higher activity compared to catalysts based on other transition metals. Over the past two decades, we and others have studied a wide range of ruthenium complexes displaying impressive catalytic performance for WO in terms of turnover number (TON) and turnover frequency (TOF). However, to produce practically applicable electrochemical, photochemical, or photo-electrochemical WO reactors, further improvement of the catalysts' structure to decrease the overpotential and increase the WO rate is of utmost importance. WO reaction, that is, the production of molecular oxygen and protons from water, requires the formation of an O-O bond through the orchestration of multiple proton and electron transfers. Promotion of these processes using redox noninnocent ligand frameworks that can accept and transfer electrons has therefore attracted substantial attention. The strategic modifications of the ligand structure in ruthenium complexes to enable proton-coupled electron transfer (PCET) and atom proton transfer (APT; in the context of WO, it is the oxygen atom (metal oxo) transfer to the oxygen atom of a water molecule in concert with proton transfer to another water molecule) to facilitate the O-O bond formation have played a central role in these efforts. In particular, promising results have been obtained with ligand frameworks containing carboxylic acid groups that either are directly bonded to the metal center or reside in the close vicinity. The improvement of redox and chemical properties of the catalysts by introduction of carboxylate groups in the ligands has proven to be quite general as demonstrated for a range of mono- and dinudear ruthenium complexes featuring ligand scaffolds based on pyridine, imidazole, and pyridazine cores. In the first coordination sphere, the carboxylate groups are firmly coordinated to the metal center as negatively charged ligands, improving the stability of the complexes and preventing metal leaching during catalysis. Another important phenomenon is the reduction of the potentials required for the formation of higher valent intermediates, especially metal-oxo species, which take active part in the key O-O bond formation step. Furthermore, the free carboxylic acid/carboxylate units in the proximity to the active center have shown exciting proton donor/acceptor properties (through PCET or APT, chemically noninnocent) that can dramatically improve the rate as well as the overpotential of the WO reaction.
9.	Das, Biswanath, et al. (författare) Water oxidation catalyzed by molecular di- and nonanuclear Fe complexes: importance of a proper ligand framework 2016 Ingår i: Dalton Transactions. - : ROYAL SOC CHEMISTRY. - 1477-9226 .- 1477-9234. ; 45:34, s. 13289-13293 Tidskriftsartikel (refereegranskat)abstract The synthesis of two molecular iron complexes, a dinuclear iron(III,III) complex and a nonanuclear iron complex, based on the di-nucleating ligand 2,2-(2-hydroxy-5-methyl-1,3-phenylene)bis(1H-benzo[d]imidazole-4-carboxylic acid) is described. The two iron complexes were found to drive the oxidation of water by the one-electron oxidant [Ru(bpy)(3)](3+).
10.	Fedorova, Dariya D., et al. (författare) Divergent Synthesis of Natural Benzyl Salicylate and Benzyl Gentisate Glucosides 2020 Ingår i: Journal of Natural Products. - : American Chemical Society (ACS). - 0163-3864 .- 1520-6025. ; 83:10, s. 3173-3180 Tidskriftsartikel (refereegranskat)abstract Herein is reported the first total synthesis of benzyl salicylate and benzyl gentisate glucosides present in various plant species, in particular the Salix genus, such as Populus balsamifera and P. trichocarpa. The method permits the synthesis of several natural phenolic acid derivatives and their glucosides starting from salicylic or gentisic acid. The divergent approach afforded access to three different acetylated glucosides from a common synthetic intermediate. The key step in the total synthesis of naturally occurring glycosides-the selective deacetylation of the sugar moiety-was achieved in the presence of a labile benzyl ester group by employing mild deacetylation conditions. The protocol permitted synthesis of trichocarpine (4 steps, 40% overall yield), isotrichocarpine (3 steps, 51% overall yield), trichoside (6 steps, 40% overall yield), and deoxytrichocarpine (3 steps, 42% overall yield) for the first time (>95% purity). Also, the optimized mild deacetylation conditions allowed synthesis of 2-O-acetylated derivatives of all four glycosides (5-17% overall yield, 90-95% purity), which are rare plant metabolites.
11.	Geng, Xin, et al. (författare) Construction of Phenanthridinone Skeletons through Palladium-Catalyzed Annulation 2023 Ingår i: Journal of Organic Chemistry. - : American Chemical Society (ACS). - 0022-3263 .- 1520-6904. ; 88:17, s. 12738-12743 Tidskriftsartikel (refereegranskat)abstract Herein, a straightforward synthetic approach for the construction of phenanthridin-6(5H)-one skeletons is disclosed. The developed protocol relies on palladium catalysis, providing controlled access to a range of functionalized phenanthridin-6(5H)-ones in 59-88% yields. Furthermore, plausible reaction pathways are proposed based on mechanistic experiments.
12.	Geng, Xin, et al. (författare) Tandem Palladium/Copper-Catalyzed Decarboxylative Approach to Benzoimidazo- and Imidazophenanthridine Skeletons 2022 Ingår i: Organic Letters. - : American Chemical Society (ACS). - 1523-7060 .- 1523-7052. ; 24:50, s. 9194-9199 Tidskriftsartikel (refereegranskat)abstract A protocol for a tandem Pd/Cu-catalyzed intermolecular cross-coupling cascade between o-bromobenzoic acids and 2-(2-bromoaryl)-1H-benzo[d]imidazoles or the corresponding imidazoles is presented. The protocol provides conceptually novel and controlled access to synthetically useful N-fused (benzo)imidazophenanthridine scaffolds with high efficiency, a broad substrate scope, and excellent functional group compatibility.
13.	Gustafson, Karl P. J., et al. (författare) Water oxidation mediated by ruthenium oxide nanoparticles supported on siliceous mesocellular foam 2017 Ingår i: Catalysis Science & Technology. - : Royal Society of Chemistry. - 2044-4753 .- 2044-4761. ; 7:1, s. 293-299 Tidskriftsartikel (refereegranskat)abstract Artificial photosynthesis is an attractive strategy for converting solar energy into fuel. In this context, development of catalysts for oxidation of water to molecular oxygen remains a critical bottleneck. Herein, we describe the preparation of a well-defined nanostructured RuO2 catalyst, which is able to carry out the oxidation of water both chemically and photochemically. The developed heterogeneous RuO2 nanocatalyst was found to be highly active, exceeding the performance of most known heterogeneous water oxidation catalysts when driven by chemical or photogenerated oxidants.
14.	Huang, M. -Q, et al. (författare) Switchable Copper-Catalyzed Approach to Benzodithiole, Benzothiaselenole, and Dibenzodithiocine Skeletons 2020 Ingår i: Organic Letters. - : American Chemical Society (ACS). - 1523-7060 .- 1523-7052. ; 22:9, s. 3454-3459 Tidskriftsartikel (refereegranskat)abstract A copper-catalyzed reaction between 2-bromo-benzothioamides and S8 or Se involving sulfur rearrangement is reported, enabling access to benzodithioles 2 and benzothiaselenoles 6 in the presence of Cs2CO3. In the absence of S8 or Se, the reaction affords dibenzodithiocines 7 via two consecutive C(sp2)-S Ullmann couplings.
15.	Iqbal, M. Naeem, et al. (författare) Mesoporous Ruthenium Oxide : A Heterogeneous Catalyst for Water Oxidation 2017 Ingår i: ACS Sustainable Chemistry and Engineering. - : American Chemical Society (ACS). - 2168-0485. ; 5:11, s. 9651-9656 Tidskriftsartikel (refereegranskat)abstract Herein we report the synthesis of mesoporous ruthenium oxide (MP-RuO2) using a template-based approach. The catalytic efficiency of the prepared MP-RuO2 was compared to commercially available ruthenium oxide nanoparticles (C-RuO2) as heterogeneous catalysts for water oxidation. The results demonstrated superior performance of MP-RuO2 for oxygen evolution compared to the C-RuO2 with respect to recyclability, amount of generated oxygen, and stability over several catalytic runs.
16.	Li, L., et al. (författare) Ruthenium containing molecular electrocatalyst on glassy carbon for electrochemical water splitting 2022 Ingår i: Dalton Transactions. - : Royal Society of Chemistry (RSC). - 1477-9226 .- 1477-9234. ; 51:20, s. 7957-7965 Tidskriftsartikel (refereegranskat)abstract Electrochemical water splitting constitutes one of the most promising strategies for converting water into hydrogen-based fuels, and this technology is predicted to play a key role in the transition towards a carbon-neutral energy economy. To enable the design of cost-effective electrolysis cells based on this technology, new and more efficient anodes with augmented water splitting activity and stability will be required. Herein, we report an active molecular Ru-based catalyst for electrochemically-driven water oxidation (overpotential of ∼395 mV at pH 7 phosphate buffer) and two simple methods for preparing anodes by attaching this catalyst onto glassy carbon through multi-walled carbon nanotubes to improve stability as well as reactivity. The anodes modified with the molecular catalyst were characterized by a broad toolbox of microscopy and spectroscopy techniques, and interestingly no RuO2 formation was detected during electrocatalysis over 4 h. These results demonstrate that the herein presented strategy can be used to prepare anodes that rival the performance of state-of-the-art metal oxide anodes.
17.	Liu, Jianquan, et al. (författare) Closing the radical gap in chemical synthesis 2020 Ingår i: Science. - : American Association for the Advancement of Science (AAAS). - 0036-8075 .- 1095-9203. ; 368:6497, s. 1312-1313 Tidskriftsartikel (övrigt vetenskapligt/konstnärligt)abstract Unstable radical intermediates are harnessed in a microfluidic electrochemical cell
18.	Liu, Jian-Quan, et al. (författare) Recent Advances in Photoredox Catalysis Enabled Functionalization of alpha-Amino Acids and Peptides : Concepts, Strategies and Mechanisms 2019 Ingår i: Synthesis (Stuttgart). - : GEORG THIEME VERLAG KG. - 0039-7881 .- 1437-210X. ; 51:14, s. 2759-2791 Forskningsöversikt (refereegranskat)abstract The selective modification of alpha-amino acids and peptides constitutes a pivotal arena for accessing new peptide-based materials and therapeutics. In recent years, visible light photoredox catalysis has appeared as a powerful platform for the activation of small molecules via single-electron transfer events, allowing previously inaccessible reaction pathways to be explored. This review outlines the recent advances, mechanistic underpinnings, and opportunities of applying photoredox catalysis to the expansion of the synthetic repertoire for the modification of specific amino acid residues. 1 Introduction 2 Visible-Light-Mediated Functionalization of alpha-Amino Acids 2.1 Decarboxylative Functionalization Involving Redox-Active Esters 2.2 Direct Decarboxylative Coupling Strategies 2.3 Hypervalent Iodine Reagents 2.4 Dual Photoredox and Transition-Metal Catalysis 2.5 Amination and Deamination Strategies 3 Photoinduced Peptide Diversification 3.1 Gese-Type Bioconjugation Methods 3.2 Peptide Macrocyclization through Photoredox Catalysis 3.3 Biomolecule Conjugation through Arylation 3.4 C-H Functionalization Manifolds 4 Conclusions and Outlook
19.	Liu, Jian-Quan, et al. (författare) Silver-Induced [3+2] Cycloaddition of Isocyanides with Acyl Chlorides : Regioselective Synthesis of 2,5-Disubstituted Oxazoles 2019 Ingår i: ChemCatChem. - : John Wiley & Sons. - 1867-3880 .- 1867-3899. ; 11:17, s. 4272-4275 Tidskriftsartikel (refereegranskat)abstract A silver-induced cycloaddition of isocyanides with acyl chlorides has been developed. This transition metal-catalyzed strategy provides an effective and scalable approach for the formation of 2,5-disubstituted oxazoles in good to high yields. The employed silver-based MOF catalyst can be efficiently recycled without compromising the yield.
20.	Liu, Jian Quan, et al. (författare) Silver-Mediated Synthesis of Substituted Benzofuran- and Indole-Pyrroles via Sequential Reaction of ortho-Alkynylaromatics with Methylene Isocyanides 2019 Ingår i: Journal of Organic Chemistry. - : American Chemical Society (ACS). - 0022-3263 .- 1520-6904. ; 84:14, s. 8998-9006 Tidskriftsartikel (refereegranskat)abstract A silver-mediated reaction between 2-ethynyl-3-(1-hydroxyprop-2-yn-1-yl)phenols or 2-ethyn-yl-3-(1-hydroxy-prop-2-yn-1-yl)anilines and methylene isocyanides has been developed. A sequential 5-endo-dig cyclization and [3 + 2] cycloaddition process is proposed. This synthetic strategy is atom- and step-efficient and applicable to a broad scope of substrates, allowing the synthesis of valuable substituted benzofuran- and indole-pyrroles in moderate to high yields.
21.	Lv, L., et al. (författare) Silver-Catalyzed [3+1+1] Annulation of Nitrones with Isocyanoacetates as an Approach to 1,4,5-Trisubstituted Imidazoles 2021 Ingår i: European Journal of Organic Chemistry. - : Wiley. - 1434-193X .- 1099-0690. ; 2021:6, s. 964-968 Tidskriftsartikel (refereegranskat)abstract A silver-catalyzed protocol for [3+1+1] annulation of nitrones and isocyanoacetates is reported. The reaction is proposed to proceed through sequential [3+2] cycloaddition, ring-opening, cyclization-oxidation, and dealkylation, allowing access to a broad scope of valuable polysubstituted imidazoles in high yields.
22.	Olsen, Peter, et al. (författare) Cyclic allylic carbonates as a renewable platform for protecting chemistry in water 2018 Ingår i: Green Chemistry. - : Royal Society of Chemistry (RSC). - 1463-9262 .- 1463-9270. ; 20:14, s. 3186-3190 Tidskriftsartikel (refereegranskat)abstract The present work explores different cyclic allylic carbonates as a potential class of allylcarbamate precursors. The 5-membered carbonate formed a carbamate with very good thermal and pH stability, which could be cleanly deprotected in aqueous solution, in just 30 min with 2 mol% Pd(OAc)(2) as catalyst. The polar nature of the installed motif made it possible to deprotect highly unpolar substrates in water as solvent.
23.	Shatskiy, Andrey, et al. (författare) Back cover 2021 Ingår i: Chemical Science. - : Royal Society of Chemistry (RSC). - 2041-6520 .- 2041-6539. ; 12:15, s. 5430-5437 Tidskriftsartikel (refereegranskat)
24.	Shatskiy, Andrey, 1989-, et al. (författare) Biomass Processing via Photochemical Means 2021 Ingår i: Biomass Valorization. - : Wiley. ; , s. 265-288 Bokkapitel (övrigt vetenskapligt/konstnärligt)abstract Biomass has emerged as a promising renewable source for production of platform chemicals, fuels, and materials. Lignin, an irregular structure and water-insoluble polymer, is the largest renewable feedstock for aromatic building blocks and materials. Photoredox-based reaction strategies have emerged as a powerful platform for harnessing the unique reactivity of open-shell intermediates, such as radicals and radical ions. Various strategies for photochemical valorization of biomass have been presented. The proton-coupled electron transfer reactions have also found a variety of practical applications in synthetic chemistry, furnishing a number of indispensable reaction manifolds. This chapter focuses on molecularly defined catalytic systems for valorization of lignin activated by visible light. A series of photocatalysts with varying oxidative/reductive power was synthesized by copolymerization of carbazole-derived donor and acceptor monomers in different ratios via Fe-catalyzed oxidative polymerization. The photocatalytic reduction of the N-O bond in the acyl oximes was achieved with a phenothiazine-based photocatalyst.
25.	Shatskiy, Andrey, et al. (författare) Catalyst-solvent interactions in a dinuclear Ru-based water oxidation catalyst 2016 Ingår i: Dalton Transactions. - : Royal Society of Chemistry (RSC). - 1477-9226 .- 1477-9234. ; 45:47, s. 19024-19033 Tidskriftsartikel (refereegranskat)abstract Photocatalytic water oxidation represents a key process in conversion of solar energy into fuels and can be facilitated by the use of molecular transition metal-based catalysts. A novel straightforward approach for covalent linking of the catalytic units to other moieties is demonstrated by preparation of a dinuclear complex containing two [Ru(pdc)(pic)(3)]-derived units (pdc = 2,6-pyridinedicarboxylate, pic = 4-picoline). The activity of this complex towards chemical and photochemical oxidation of water was evaluated and a detailed insight is given into the interactions between the catalyst and acetonitrile, a common co-solvent employed to increase solubility of water oxidation catalysts. The solvent-induced transformations were studied by electrochemical and spectroscopic techniques and the relevant quantitative parameters were extracted.
26.	Shatskiy, Andrey, et al. (författare) Chemodivergent difunctionalization of alkenes through base-controlled radical relay 2022 Ingår i: Chem. - : Elsevier BV. - 2451-9308 .- 2451-9294. ; 8:1, s. 12-14 Tidskriftsartikel (refereegranskat)abstract Establishing chemodivergent synthetic strategies remains a daunting task in the realm of free-radical reaction manifolds. In the December issue of Chem, Glorius and co-workers resolve this challenge for selective difunctionalization of aliphatic alkenes. In the disclosed light-promoted radical relay process, switchable trifluoromethylation/alkylation or trifluoromethylation/sulfonylation of alkenes is achieved.
27.	Shatskiy, Andrey, et al. (författare) Controlling Radical Relay Processes with Visible Light 2021 Ingår i: Chem. - : Cell Press. - 2451-9308 .- 2451-9294. ; 7:2, s. 283-285 Tidskriftsartikel (övrigt vetenskapligt/konstnärligt)abstract Harnessing free radical intermediates for selective functionalization of organic compounds has been widely demonstrated under photocatalytic conditions requiring a distinct photocatalyst. In this issue of Chem, Seo, Chang, and co-workers demonstrate an alternative photocatalyst- free light-mediated approach that allows efficient amidation of aldehydes via N-centered radical intermediate.
28.	Shatskiy, Andrey, et al. (författare) Electrifying catalytic aerobic oxidation 2021 Ingår i: NATURE CATALYSIS. - : Springer Nature. - 2520-1158. ; 4:2, s. 96-97 Tidskriftsartikel (övrigt vetenskapligt/konstnärligt)
29.	Shatskiy, Andrey, 1989-, et al. (författare) Exploiting photoredox catalysis for carbohydrate modification through C–H and C–C bond activation 2022 Ingår i: Nature Reviews Chemistry. - : Springer Nature. - 2397-3358. ; 6:11, s. 782-805 Tidskriftsartikel (refereegranskat)abstract Photoredox catalysis has recently emerged as a powerful synthetic platform for accessing complex chemical structures through non-traditional bond disconnection strategies that proceed through free-radical intermediates. Such synthetic strategies have been used for a range of organic transformations; however, in carbohydrate chemistry they have primarily been applied to the generation of oxocarbenium ion intermediates in the ubiquitous glycosylation reaction. In this Review, we present more intricate light-induced synthetic strategies to modify native carbohydrates through homolytic C–H and C–C bond cleavage. These strategies allow access to glycans and glycoconjugates with profoundly altered carbohydrate skeletons, which are challenging to obtain through conventional synthetic means. Carbohydrate derivatives with such structural motifs represent a broad class of natural products integral to numerous biochemical processes and can be found in active pharmaceutical substances. Here we present progress made in C–H and C–C bond activation of carbohydrates through photoredox catalysis, focusing on the operational mechanisms and the scope of the described methodologies. [Figure not available: see fulltext.].
30.	Shatskiy, Andrey, 1989- (författare) Highly Active Ruthenium-Based Water Oxidation Catalyst with an Easy Access to the Catalytically Active Species Annan publikation (övrigt vetenskapligt/konstnärligt)abstract Herein is described a highly active ruthenium-based water oxidation catalyst [RuIV(mcbp)(O)(py)2] (5, mcbp2− = 2,6-bis(1-methyl-4-(carboxylate)benzimidazol-2-yl)pyridine), which can be generated from either [RuII(mcbp)(py)2] (4II) or [RuIII(Hmcbp)(py)2]2+ (4III). Complexes 4II and 4III were isolated and characterized by single crystal X-ray analysis, NMR, UV-vis, FT-IR, ESI-HRMS, EPR, and elemental analysis, and their redox properties were studied in detail by electrochemical and spectroscopic methods. Unlike for the parent catalyst [Ru(tda)(py)2] (1, tda2− = [2,2′:6′,2″-terpyridine]-6,6″-dicarboxylate), for which full transformation to the catalytically active species [RuIV(tda)(O)(py)2] (2) could not be carried out — stoichiometric generation of the catalytically active Ru-aqua complex 5 from 4II was achieved under mild conditions (pH 7.0) and short reaction times. The redox properties of the catalyst were studied and its activity for electrocatalytic water oxidation was evaluated, reaching TOFmax ≈ 40 000 s−1 at pH 9.0 (from the foot-of-the-wave analysis, FOWA), which is comparable to the activity of the state-of-the-art catalyst 2.
31.	Shatskiy, Andrey, et al. (författare) Organic Electrosynthesis : Applications in Complex Molecule Synthesis 2019 Ingår i: ChemElectroChem. - : Wiley-VCH Verlagsgesellschaft. - 2196-0216. ; 6:16, s. 4067-4092 Tidskriftsartikel (refereegranskat)abstract Organic electrosynthesis is an enabling and sustainable technology, which constitutes a rapidly expanding field of research. Electrochemical approaches serve as convenient and green alternatives to stoichiometric and toxic chemical redox agents. Electrosynthesis constitutes a promising platform for harnessing the unique reactivity profiles of radical intermediates, expediting the development of new reaction manifolds. This Review highlights both anodic and cathodic methods for the construction of various kinds of complex molecules.
32.	Shatskiy, Andrey, 1989-, et al. (författare) Photoredox-Enabled Decarboxylative Synthesis of Unnatural α-Amino Acids 2022 Ingår i: Synlett. - : Georg Thieme Verlag KG. - 0936-5214 .- 1437-2096. ; 33:2, s. 109-115 Tidskriftsartikel (refereegranskat)abstract Recently, development of general synthetic routes to unnatural α-amino acids has gained significant momentum, driven by the high demand for such building blocks in fundamental research within molecular and structural biology, as well as for development of new pharmaceuticals. Herein, we highlight the recent progress in employing photoredox-mediated synthetic methods for accessing unnatural α-amino acids with a focus on various decarboxylative radical-based strategies.
33.	Shatskiy, Andrey, 1989- (författare) Ru-Based Water Oxidation Catalysts : Development and Mechanistic Studies 2018 Doktorsavhandling (övrigt vetenskapligt/konstnärligt)abstract Oxidation of water constitutes one of the most challenging processes in artificial photosynthesis, which aims at storing solar energy in the form of chemical bonds of high-energy fuels. To facilitate this process, efficient and durable water oxidation catalysts have to be developed and integrated into the complete photosynthetic cells. Importantly, the intricate complexity of such devices requires the catalyst not only to be highly efficient and robust, but also operate through a well-defined mechanism.This thesis describes the development and mechanistic studies of new water oxidation catalysts based on ruthenium. The first part of the thesis describes the synthesis of a dinuclear ruthenium-based catalyst active for both chemical and light-driven water oxidation. This catalyst displayed a pronounced influence of the acetonitrile co-solvent on the redox properties, which was studied in detail by electrochemical methods. In the second part, a new benzimidazole-based mononuclear catalyst was evaluated. The activity of the catalyst was studied for chemical and light-driven water oxidation, and insight into the operating mechanism was provided with the help of density functional theory calculations. In the third part of the thesis, a new mononuclear ruthenium-based catalyst was prepared and evaluated for electrochemically-driven water oxidation. This catalyst displayed activity similar to that of the current state-of-the-art water oxidation catalyst, while eliminating its main drawback, that is incomplete activation. The redox properties of the new catalyst were studied in detail by electrochemical and spectroscopic techniques, providing insight into the origins of its improved performance. Finally, in the fourth part of the thesis, a heterogeneous nanoparticulate catalyst immobilized on a solid support is described. The catalyst displayed high activity and stability during chemical and light-driven water oxidation, which was attributed to the small average particle size and efficient anchoring of the catalyst to the heterogeneous support via an oxidatively-stable linker.
34.	Shatskiy, Andrey, et al. (författare) Ruthenium-Catalyzed Asymmetric Transfer Hydrogenation of Propargylic Ketones 2015 Ingår i: ChemCatChem. - : Wiley. - 1867-3880 .- 1867-3899. ; 7:23, s. 3818-3821 Tidskriftsartikel (refereegranskat)abstract The asymmetric transfer hydrogenation of alpha,beta-propargyl ketones catalyzed by an in situ formed ruthenium-hydroxyamide complex was explored. The acetylenic alcohols were isolated in good to excellent yields with excellent ee values (typically >90%) after short reaction times at room temperature.
35.	Shatskiy, Andrey, 1989-, et al. (författare) Stereoselective synthesis of unnatural α-amino acid derivatives through photoredox catalysis 2021 Ingår i: Chemical Science. - : Royal Society of Chemistry. - 2041-6520 .- 2041-6539. ; 12:15, s. 5430-5437 Tidskriftsartikel (refereegranskat)abstract A protocol for stereoselective C-radical addition to a chiral glyoxylate-derived N-sulfinyl imine was developed through visible light-promoted photoredox catalysis, providing a convenient method for the synthesis of unnatural α-amino acids. The developed protocol allows the use of ubiquitous carboxylic acids as radical precursors without prior derivatization. The protocol utilizes near-stoichiometric amounts of the imine and the acid radical precursor in combination with a catalytic amount of an organic acridinium-based photocatalyst. Alternative mechanisms for the developed transformation are discussed and corroborated by experimental and computational studies.
36.	Shatskiy, Andrey, et al. (författare) Stereoselective Synthesis of Unnatural α-Amino Acids Through Visible Light-Promoted Decarboxylative C-Radical Addition to a Glyoxylate-Derived Sulfinyl Imine Annan publikation (övrigt vetenskapligt/konstnärligt)
37.	Shatskiy, Andrey, et al. (författare) The Art of Splitting Water : Storing Energy in a Readily Available and Convenient Form 2019 Ingår i: European Journal of Inorganic Chemistry. - : Wiley-VCH Verlagsgesellschaft. - 1434-1948 .- 1099-1948 .- 1099-0682. ; :15, s. 2020-2024 Tidskriftsartikel (refereegranskat)abstract This essay for EurJIC's special issue on "Redox Catalysis for Artificial Photosynthesis" introduces the reader to the field of water oxidation using molecular catalysts. The most essential challenge our society must address during the 21st century is perhaps the realization of a system for producing sustainable energy on the global scale. Currently, there exists an urgent need to develop effective and economical carbon-neutral or carbon-free energy technologies. The production of solar fuels through water splitting constitutes a key enabling element. The construction of robust and efficient catalysts for oxidation of water is therefore essential. In this essay the progress and mechanistic considerations pertaining to molecular water oxidation catalysts are described and discussed from a personal perspective.
38.	Shen, Xuanyu, et al. (författare) Silver-Assisted [3+2] Annulation of Nitrones with Isocyanides : Synthesis of 2,3,4-Trisubstituted 1,2,4-Oxadiazolidin-5-ones 2020 Ingår i: Journal of Organic Chemistry. - : AMER CHEMICAL SOC. - 0022-3263 .- 1520-6904. ; 85:5, s. 3560-3567 Tidskriftsartikel (refereegranskat)abstract A silver-assisted method for [3 + 2] annulation of nitrones with isocyanides has been developed. The developed protocol allows access to a variety of 2,3,4-trisubstituted 1,2,4-oxadiazolidin-S-one derivatives as single diastereomers in good to excellent yields using silver oxide as the catalyst and molecular oxygen as the terminal oxidant. A plausible mechanism involving a nucleophilic addition/cyclization/protodeargentation/oxidation pathway is proposed on the basis of experimental results.
39.	Villo, Piret, et al. (författare) Electrosynthetic C−O Bond Activation in Alcohols and Alcohol Derivatives 2023 Ingår i: Angewandte Chemie International Edition. - : Wiley. - 1433-7851 .- 1521-3773. ; 62:4 Forskningsöversikt (refereegranskat)abstract Alcohols and their derivatives are ubiquitous and versatile motifs in organic synthesis. Deoxygenative transformations of these compounds are often challenging due to the thermodynamic penalty associated with the cleavage of the C−O bond. However, electrochemically driven redox events have been shown to facilitate the C−O bond cleavage in alcohols and their derivatives either through direct electron transfer or through the use of electron transfer mediators and electroactive catalysts. Herein, a comprehensive overview of preparative electrochemically mediated protocols for C−O bond activation and functionalization is detailed, including direct and indirect electrosynthetic methods, as well as photoelectrochemical strategies.
40.	Wang, Y. -C, et al. (författare) Copper-assisted Wittig-type olefination of aldehydes with p-toluenesulfonylmethyl isocyanide 2022 Ingår i: Organic Chemistry Frontiers. - : Royal Society of Chemistry (RSC). - 2052-4110 .- 2052-4129. ; 9:15, s. 4158-4163 Tidskriftsartikel (refereegranskat)abstract The Wittig reaction is a valuable and powerful tool in organic synthesis, providing a convenient route from aldehydes and ketones to alkenes. Herein, a novel copper-assisted Wittig-type olefination of aldehydes with p-toluenesulfonylmethyl isocyanide (TosMIC) is disclosed, providing a direct and operationally simple approach to (E)-vinyl sulfones under mild conditions, compatible with a multitude of common functional groups. Experimental and computational investigations imply that the reaction proceeds through an intriguing electronically-controlled (3 + 2)/retro-(3 + 2) cycloaddition pathway.
41.	Wu, H., et al. (författare) Modular synthesis of 3-substituted isocoumarinsviasilver-catalyzed aerobic oxidation/6-endoheterocyclization ofortho-alkynylbenzaldehydes 2021 Ingår i: Organic and biomolecular chemistry. - : Royal Society of Chemistry (RSC). - 1477-0520 .- 1477-0539. ; 19:30, s. 6657-6664 Tidskriftsartikel (refereegranskat)abstract A method involving silver-catalyzed aerobic oxidation/6-endoheterocyclization ofortho-alkynylbenzaldehydes to yield 3-substituted isocoumarins is described. The developed protocol allows convenient access to a range of synthetically useful 3-substituted isocoumarins and related fused heterocyclolactones in good to high yields, using silver tetrafluoroborate as the catalyst, and atmospheric oxygen as the terminal oxidant and the source of endocyclic oxygen. Mechanistic studies suggest the involvement of a free-radical pathway.
42.	Xu, L., et al. (författare) Silver-Catalyzed Controlled Intermolecular Cross-Coupling of Silyl Enol Ethers : Scalable Access to 1,4-Diketones 2022 Ingår i: Organic Letters. - : American Chemical Society (ACS). - 1523-7060 .- 1523-7052. ; 24:25, s. 4513-4518 Tidskriftsartikel (refereegranskat)abstract A protocol for silver-catalyzed controlled intermolecular cross-coupling of silyl enolates is disclosed. The protocol displays good functional group tolerance and allows efficient preparation of a series of synthetically useful 1,4-diketones. Preliminary mechanistic investigations suggest that the reaction proceeds through a one-electron process involving free radical species in which PhBr acts as the oxidant.
43.	Zhou, Chao, et al. (författare) Highly congested spiro-compounds via photoredox-mediated dearomative annulation cascade 2022 Ingår i: Communications Chemistry. - : Springer Nature. - 2399-3669. ; 5:1 Tidskriftsartikel (refereegranskat)abstract Photo-mediated radical dearomatization involving 5-exo-trig cyclizations has proven to be an important route to accessing spirocyclic compounds, whereas 6-exo-trig spirocyclization has been much less explored. In this work, a dearomative annulation cascade is realized through photoredox-mediated C-O bond activation of aromatic carboxylic acids to produce two kinds of spirocyclic frameworks. Mechanistically, the acyl radical is formed through oxidation of triphenylphosphine and subsequent C-O bond cleavage, followed by a 6-exo-trig cyclization/SET/protonation sequence to generate the spiro-chromanone products in an intramolecular manner. Furthermore, the protocol was extended to more challenging intermolecular tandem sequences consisting of C-O bond cleavage, radical addition to an alkene substrate, and 5-exo-trig cyclization to yield complex spirocyclic lactams. Photo-mediated radical dearomatization involving 5-exo-trig cyclizations has proven to be an important route to accessing spirocyclic compounds, whereas 6-exo-trig spirocyclization has been much less explored. Here, a dearomative annulation cascade is realized through a photoredox-mediated C-O bond activation of aromatic carboxylic acids to produce two kinds of spirocyclic frameworks, whereby the spirocyclizations are triggered by acyl radical formation from benzoic acids leading to spiro-chromanones via a direct intramolecular 6-exo-trig cyclization or spirocyclic lactams via an intermolecular addition/5-exo-trig cyclization cascade.

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