Papers by Viktor Zhdankin
Angewandte Chemie, Nov 4, 2005
ABSTRACT
Electrochimica Acta, Feb 1, 2021
HAL is a multidisciplinary open access archive for the deposit and dissemination of scientific re... more HAL is a multidisciplinary open access archive for the deposit and dissemination of scientific research documents, whether they are published or not. The documents may come from teaching and research institutions in France or abroad, or from public or private research centers. L'archive ouverte pluridisciplinaire HAL, est destinée au dépôt et à la diffusion de documents scientifiques de niveau recherche, publiés ou non, émanant des établissements d'enseignement et de recherche français ou étrangers, des laboratoires publics ou privés. Distributed under a Creative Commons Attribution-NonCommercial 4.0 International License
European Journal of Organic Chemistry, Nov 22, 2018
Current Organic Synthesis, Aug 10, 2016
Potassium 4-iodylbenzenesulfonate (PIBS) is a thermally stable and water soluble hypervalent iodi... more Potassium 4-iodylbenzenesulfonate (PIBS) is a thermally stable and water soluble hypervalent iodine oxidant particularly useful as a recyclable reagent for oxidative iodination of alkenes, alkynes and ketones. This reagent can be effectively recovered from the reaction mixture by treatment of the aqueous layer with Oxone at 60 o C followed by filtration of the precipitate.
Elsevier eBooks, 2010
This chapter discusses the reactivity of five-membered heterocyclic compounds, including those wi... more This chapter discusses the reactivity of five-membered heterocyclic compounds, including those with one heteroatom in the ring. It compares and contrasts the effects of the different heteroatoms in five-membered heterocyclic compounds with one heteroatom, and compares these compounds with analogous aliphatic and benzenoid derivatives. Electrophilic attack at ring heteroatoms is rare for the neutral compounds, although examples are known for thiophenes and selenophenes. However, pyrrole N-anions undergo easy reaction with electrophiles at either the N or a C atom. The most important reactions involve electrophilic attack on ring carbon atoms, a wide variety of which are known for pyrroles, furans, and thiophenes. Most frequently, such electrophilic attack is followed by proton loss, resulting in overall substitution. Several types of reactions involving cyclic transition states are known for five-membered heteroaromatic rings with one heteroatom. The five-membered ring heterocycles possess DielsAlder reactivity of varying degree. This is most pronounced in the case of furan and benzo[c]-fused heterocycles such as isoindole. In this capacity they are functioning as heterocyclic analogues of cyclopentadiene, and high DielsAlder reactivity can be correlated with low aromaticity. Extensive use can be made of palladium (and other transition metals) catalysis in these compounds, especially for the formation of carbon–carbon bonds and for N-arylation. Pyrrole, furan, and thiophene rings are thermally very stable, requiring extreme conditions for changes to occur. Photochemical scrambling of ring atoms can involve a ring-walk or a cyclopropene mechanism. Pyrroles and indoles with Grignard reagents give the corresponding hydrocarbon and partially ionic Grignard reagents derived from the pyrrole or indole.
European Journal of Organic Chemistry, 2019
An efficient oxidative cycloaddition of enaminones with nitrile oxides generated in situ from res... more An efficient oxidative cycloaddition of enaminones with nitrile oxides generated in situ from respective aldoximes using hypervalent iodine reagents has been developed. Reactions of various aldoximes with enaminones in the presence of [hydroxy(tosyloxy)iodo]benzene involved the regioselective [a]
Advanced Synthesis & Catalysis, 2017
Two powerful hypervalent iodine(V) oxidants, DMP‐OTs (1‐tosyloxy‐1,1‐diacetoxy‐1H‐1λ5‐benzo[d][1,... more Two powerful hypervalent iodine(V) oxidants, DMP‐OTs (1‐tosyloxy‐1,1‐diacetoxy‐1H‐1λ5‐benzo[d][1,2]iodoxol‐3‐one) and IBX‐OTs (1‐tosyloxy‐1‐oxo‐1H‐1λ5‐benzo[d][1,2]iodoxol‐3‐one) show high reactivity in the oxidation of structurally complex primary and secondary alcohols, which are highly functionalized polyketide or terpene fragments or steroids. The yields of the corresponding carbonyl compounds are even higher for the protocol that uses pyridine as additive. The oxidations proceed very rapidly at room temperature leaving the protective groups and π‐systems intact and affording the corresponding carbonyl compounds in good to excellent yields. Moreover, IBX‐OTs is an efficient reagent for the oxidative dehydrogenation of steroidal alcohols to the corresponding enones.magnified image
Asian Journal of Organic Chemistry, 2016
As a first example of metal‐free and catalytic fluorinative transformations of alkynes, we develo... more As a first example of metal‐free and catalytic fluorinative transformations of alkynes, we developed a cycloisomerization–fluorination sequence of N‐propargyl amides catalyzed by an iodine(III) species. The iodine(III) catalyst is in situ generated from iodoarene as a precatalyst with Selectfluor as a fluorinating oxidant in the presence of HF⋅pyridine.
Handbook of Heterocyclic Chemistry, 2010
This chapter provides an overview of the main types of reactions used in synthesis of monocyclic ... more This chapter provides an overview of the main types of reactions used in synthesis of monocyclic rings with two or more heteroatoms. It begins by discussing the preparative methods involving substituent introduction and modification for five-membered (azoles) and six-membered (azines) monocyclic compounds with various heteroatoms. The reactivity of six-membered rings containing two heteroatoms bears the same relationship to six-membered rings containing one heteroatom as do the latter to benzene, hence many of the methods for the preparation of pyridines by substituent introduction and modification are also applicable to the preparation of analogous azines. Three-membered rings with two heteroatoms (oxaziridines, diaziridines, diaziridinones, etc.) and four-membered rings with two heteroatoms (1,2-thiazetidines, 1,2-oxazetidines, 1,2-diazetidinones, 1,2-dioxetanes, etc.) are prepared by reactions such as [2 + 2] cycloaddition and cyclization of appropriate precursors. Five-membered rings with two adjacent heteroatoms, such as pyrazoles, isoxazoles, isothiazoles, etc. are most frequently made using a hydroxylamine or hydrazine derivative; however, dipolar cycloadditions are also significant. Methods forming a Z–Z bond are important particularly for sulfur-containing derivatives. The most important synthetic methods for six-membered rings such as pyridazines, 1,2-oxazines, etc. involve condensation of hydrazine, hydroxylamine, or hydrogen peroxide with a 1,4-dioxygenated carbon chain, and these procedures are particularly useful for the preparation of pyridazines and 1,2-oxazines. Other methods include Diels–Alder reactions of a diene with an azo or nitroso compound.
Chemical Society reviews, 2024
Synthesis, 2022
Hypervalent iodine (HVI) reagents have gained much attention as versatile oxidants because of the... more Hypervalent iodine (HVI) reagents have gained much attention as versatile oxidants because of their low toxicity, mild reactivity, easy handling, and availability. Despite their unique reactivity and other advantageous properties, stoichiometric HVI reagents are associated with the disadvantage of generating non-recyclable iodoarenes as waste/co-products. To overcome these drawbacks, the syntheses and utilization of various recyclable hypervalent iodine reagents have been established in recent years. This review summarizes the development of various recyclable non-polymeric, polymer-supported, ionic-liquid-supported, and metal–organic framework (MOF)-hybridized HVI reagents.1 Introduction2 Polymer-Supported Hypervalent Iodine Reagents2.1 Polymer-Supported Hypervalent Iodine(III) Reagents2.2 Polymer-Supported Hypervalent Iodine(V) Reagents3 Non-Polymeric Recyclable Hypervalent Iodine Reagents3.1 Non-Polymeric Recyclable Hypervalent Iodine(III) Reagents3.2 Recyclable Non-Polymeric Hyp...
Beilstein Journal of Organic Chemistry, Apr 12, 2018
This article is part of the Thematic Series "Hypervalent iodine chemistry in organic synthesis".
ChemInform, 1989
Cyclohexene (I) or the dihydropyran (III) react with phenyliodonium sulfate or the iodosobenzene‐... more Cyclohexene (I) or the dihydropyran (III) react with phenyliodonium sulfate or the iodosobenzene‐boron trifluoride complex under ring contraction to give the aldehydes (II) or (IV).
Chemischer Informationsdienst, 1984
Chemischer Informationsdienst, 1983
ChemInform Abstract Bei der Halogenierung der Alkene (I) in Gegenwart der Tetrabutylammoniumsulfo... more ChemInform Abstract Bei der Halogenierung der Alkene (I) in Gegenwart der Tetrabutylammoniumsulfonate (II) entstehen neben den Produkten der Halogenaddition (III) (keine Ausb.-Angabe) die β-halogensubstituierten Tosylate bzw. Mesylate (IV). Dieses Verfahren kann zur Darstellung neuer β-Halogenester von aliphatischen oder aromatischen Sulfonsäuren dienen.
Handbook of Heterocyclic Chemistry, 2010
Publisher Summary This chapter focuses on five-membered heterocyclic compounds with two or more h... more Publisher Summary This chapter focuses on five-membered heterocyclic compounds with two or more heteroatoms and discusses their possible structures, nomenclature, properties, and tautomerism. Systematic replacement of CH by N leads to nine additional monocyclic heteroaromatic nitrogen systems, which are known collectively as azoles. Reduction of one or two double bonds in the azole ring gives nonaromatic systems, which have been described as azolines and azolidines. Each of the aromatic azolium cations can be converted into a neutral system by substitution of an anionic O, S, or NR group on to a ring carbon atom. Examples of oxygen and sulfur rings with exocyclic conjugation systems are the 1,2-dithiole-3-thione and the type A mesoionic 1,3-thiazolium-4-olate. Isoxazole, thiazole, and their derivatives are examples of five-membered heterocyclics when ring atoms can be chosen from oxygen, sulfur, and nitrogen. The chapter presents the findings of research studies on the intermolecular forces between five-membered heterocyclic molecules and their influence on melting and boiling points, solubilities, and chromatographic properties, their thermochemistry, conformations of saturated ring systems, and aromaticity. Overall, the aromaticity of azoles is intermediate between that of five-membered heterocycles with one heteroatom and six-membered heterocycles (azines). Furthermore, types of tautomerism in five-membered heterocyclic compounds with two or more heteroatoms, including prototropic tautomerism, ring-chain tautomerism, and valence tautomerism are discussed.
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Papers by Viktor Zhdankin