Relevant bibliographies by topics / Hypervalent iodine

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Academic literature on the topic 'Hypervalent iodine'

Author: Grafiati
Published: 4 June 2021
Last updated: 30 November 2024

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Journal articles on the topic "Hypervalent iodine"

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Zhang, Chi, Xiao-Guang Yang, Ze-Nan Hu, Meng-Cheng Jia, and Feng-Huan Du. "Recent Advances and the Prospect of Hypervalent Iodine Chemistry." Synlett 32, no. 13 (April 27, 2021): 1289–96. http://dx.doi.org/10.1055/a-1492-4943.

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AbstractNowadays, hypervalent iodine chemistry has remarkably advanced in parallel with the emergence of novel hypervalent iodine reagents. Hypervalent iodine reagents, due to their outstanding characteristics including rich reactivities, excellent chemoselectivity, stability, and environmental friendliness, are becoming more and more popular in the synthetic organic chemistry. In this Account, a number of recent elegant research works and our perspective on the future of hypervalent iodine chemistry is presented.1 Introduction2 Recent Advances and Discussion2.1 Novel Reactivities of Hypervalent Iodine Reagents2.2 Atom-Economical Reactions Promoted by Hypervalent Iodine Reagents2.3 Other Applications of Hypervalent Iodine Reagents2.4 The Applications of DFT Calculations in Elucidating Reaction Mechanism Involving Hypervalent Iodine Reagents3 Outlook and Conclusion
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Mowdawalla, Cyrus, Faiz Ahmed, Tian Li, Kiet Pham, Loma Dave, Grace Kim, and I. F. Dempsey Hyatt. "Hypervalent iodine-guided electrophilic substitution: para-selective substitution across aryl iodonium compounds with benzyl groups." Beilstein Journal of Organic Chemistry 14 (May 14, 2018): 1039–45. http://dx.doi.org/10.3762/bjoc.14.91.

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The reactivity of benzyl hypervalent iodine intermediates was explored in congruence with the reductive iodonio-Claisen rearrangement (RICR) to show that there may be an underlying mechanism which expands the reasoning behind the previously known C–C bond-forming reaction. By rationalizing the hypervalent iodine’s metal-like properties it was concluded that a transmetallation mechanism could be occurring with metalloid groups such as silicon and boron. Hypervalent iodine reagents such as Zefirov’s reagent, cyclic iodonium reagents, iodosobenzene/BF3, and PhI(OAc)2/BF3 or triflate-based activators were tested. A desirable facet of the reported reaction is that iodine(I) is incorporated into the product thus providing greater atom economy and a valuable functional group handle for further transformations. The altering of the RICR’s ortho-selectivity to form para-selective products with benzyl hypervalent iodine intermediates suggests a mechanism that involves hypervalent iodine-guided electrophilic substitution (HIGES).
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Kupwade, Ravindra V. "A Concise Review of Hypervalent Iodine with Special Reference to Dess- Martin Periodinane." Mini-Reviews in Organic Chemistry 17, no. 8 (December 24, 2020): 946–57. http://dx.doi.org/10.2174/1570193x17666200221124739.

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The chemistry of hypervalent iodine compounds has been experiencing considerable attention of organic chemists during the past few years. Hypervalent iodine reagents have found ubiquitous applications in organic synthesis because of their mild and highly chemoselective oxidizing properties, easy commercial availability, and environmental benign character. Along with oxidation of alcohol, they have also shown to be useful in number of organic transformations which include oxidative functionalization of carbonyl compounds, catalytic imidations, cyclization, oxidative coupling of phenols, amines and related compounds. Among various hypervalent iodine reagents, iodine-V compounds (λ5-iodanes) have attracted much attention in recent years. This review narrates the particular advances in iodine (V) reagents with special emphasis on the use of DMP in organic transformations.
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Yoshimura, Akira, Akio Saito, Viktor V. Zhdankin, and Mekhman S. Yusubov. "Synthesis of Oxazoline and Oxazole Derivatives by Hypervalent-Iodine-Mediated Oxidative Cycloaddition Reactions." Synthesis 52, no. 16 (May 18, 2020): 2299–310. http://dx.doi.org/10.1055/s-0040-1707122.

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Organohypervalent iodine reagents are widely used for the preparation of various oxazolines, oxazoles, isoxazolines, and isoxazoles. In the formation of these heterocyclic compounds, hypervalent iodine species can serve as the activating reagents for various substrates, as well as the heteroatom donor reagents. In recent research, both chemical and electrochemical approaches toward generation of hypervalent iodine species have been utilized. The in situ generated active species can react with appropriate substrates to give the corresponding heterocyclic products. In this short review, we summarize the hypervalent-iodine­-mediated preparation of oxazolines, oxazoles, isoxazolines, and isoxazoles starting from various substrates.1 Introduction2 Synthesis of Oxazolines3 Synthesis of Oxazoles4 Synthesis of Isoxazolines5 Synthesis of Isoxazoles6 Conclusion
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Yannacone, Seth, Vytor Oliveira, Niraj Verma, and Elfi Kraka. "A Continuum from Halogen Bonds to Covalent Bonds: Where Do λ3 Iodanes Fit?" Inorganics 7, no. 4 (March 28, 2019): 47. http://dx.doi.org/10.3390/inorganics7040047.

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The intrinsic bonding nature of λ 3 -iodanes was investigated to determine where its hypervalent bonds fit along the spectrum between halogen bonding and covalent bonding. Density functional theory with an augmented Dunning valence triple zeta basis set ( ω B97X-D/aug-cc-pVTZ) coupled with vibrational spectroscopy was utilized to study a diverse set of 34 hypervalent iodine compounds. This level of theory was rationalized by comparing computational and experimental data for a small set of closely-related and well-studied iodine molecules and by a comparison with CCSD(T)/aug-cc-pVTZ results for a subset of the investigated iodine compounds. Axial bonds in λ 3 -iodanes fit between the three-center four-electron bond, as observed for the trihalide species IF 2 − and the covalent FI molecule. The equatorial bonds in λ 3 -iodanes are of a covalent nature. We explored how the equatorial ligand and axial substituents affect the chemical properties of λ 3 -iodanes by analyzing natural bond orbital charges, local vibrational modes, the covalent/electrostatic character, and the three-center four-electron bonding character. In summary, our results show for the first time that there is a smooth transition between halogen bonding → 3c–4e bonding in trihalides → 3c–4e bonding in hypervalent iodine compounds → covalent bonding, opening a manifold of new avenues for the design of hypervalent iodine compounds with specific properties.
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Dearman, Samuel M. G., Xiang Li, Yang Li, Kuldip Singh, and Alison M. Stuart. "Oxidative fluorination with Selectfluor: A convenient procedure for preparing hypervalent iodine(V) fluorides." Beilstein Journal of Organic Chemistry 20 (July 29, 2024): 1785–93. http://dx.doi.org/10.3762/bjoc.20.157.

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The ability to investigate hypervalent iodine(V) fluorides has been limited primarily by their difficult preparation traditionally using harsh fluorinating reagents such as trifluoromethyl hypofluorite and bromine trifluoride. Here, we report a mild and efficient route using Selectfluor to deliver hypervalent iodine(V) fluorides in good isolated yields (72–90%). Stability studies revealed that bicyclic difluoro(aryl)-λ5-iodane 6 was much more stable in acetonitrile-d3 than in chloroform-d1, presumably due to acetonitrile coordinating to the iodine(V) centre and stabilising it via halogen bonding.
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Kiyokawa, Kensuke, and Satoshi Minakata. "Iodine-Based Reagents in Oxidative Amination and Oxygenation." Synlett 31, no. 09 (February 26, 2020): 845–55. http://dx.doi.org/10.1055/s-0039-1690827.

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In this Account, we provide an overview of our recent advances in oxidative transformations that enable the introduction of nitrogen and oxygen functionalities into organic molecules by taking advantage of the unique characteristics of iodine-based reagents, such as hypervalency, soft Lewis acidity, high leaving ability, and radical reactivity. We also report on the development of new types of hypervalent iodine reagents containing a transferable nitrogen functional group with the objective of preparing primary amines, which is described in the latter part of this Account.1 Introduction2 Decarboxylative Functionalization of β,γ-Unsaturated Carboxylic Acids3 Decarboxylative Functionalization at Tertiary Carbon Centers4 C–H Bond Functionalization at Tertiary Carbon Centers5 Intramolecular C–H Amination of Sulfamate Esters and N-Alkylsulfamides6 Oxidative Amination with Hypervalent Iodine Reagents Containing Transferable Nitrogen Functional Groups7 Summary and Outlook
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Kotali, Antigoni. "Hypervalent Iodine." Molecules 10, no. 1 (January 31, 2005): 181–82. http://dx.doi.org/10.3390/10010181.

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Maegawa, Tomohiro, Yasuyoshi Miki, Ryohei Oishi, Kazutoshi Segi, Hiromi Hamamoto, and Akira Nakamura. "Hypervalent Iodine-Mediated Beckmann Rearrangement of Ketoximes." Synlett 29, no. 11 (April 23, 2018): 1465–68. http://dx.doi.org/10.1055/s-0037-1609686.

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We developed a Beckmann rearrangement employing hypervalent iodine reagent under mild conditions. The reaction of ketoxime with hypervalent iodine afforded the corresponding ketone, but premixing of hypervalent iodine and a Lewis acid was effective for promoting Beckmann rearrangement. Aromatic and aliphatic ketoximes were converted into their corresponding amides in good to high yields.
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Zhdankin, V. "APPLICATION OF HYPERVALENT IODINE COMPOUNDS IN ADVANCED GREEN TECHNOLOGIES." Resource-Efficient Technologies, no. 1 (May 14, 2021): 1–16. http://dx.doi.org/10.18799/24056529/2021/1/286.

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This review summarizes industrial applications of inorganic and organic polyvalent (hypervalent) iodine compounds. Inorganic iodate salts have found some application as a dietary supplements and food additives. Iodine pentafluoride is used as industrial fluorinating reagent, and iodine pentoxide is a powerful and selective oxidant that is particularly useful in analytical chemistry. Common organic hypervalent iodine reagents such as (dichloroiodo)benzene and (diacetoxyiodo)benzene are occasionally used in chemical industry as the reagents for production of important pharmaceutical intermediates. Iodonium salts have found industrial application as photoinitiators for cationic photopolymerizations. Various iodonium compounds are widely used as precursors to [18F]-fluorinated radiotracers in the Positron Emission Tomography (PET).
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Dissertations / Theses on the topic "Hypervalent iodine"

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Khan, Zulfiqar Ali. "Novel iodine mediated carbocyclisations and hypervalent iodine(III) reagents." Thesis, Cardiff University, 2010. http://orca.cf.ac.uk/54137/.

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The first chapter focuses on the introduction of iodine mediated carbocyclisations and their applications continue to present a stimulating challenge in target- and diversity-oriented synthesis. The second chapter discusses applications and brief literature overview about classical approaches towards the syntheses of indene derivatives. Herein the syntheses of 3-iodo-1 H-indene derivatives via iodonium-promoted 5-endo-dig carbocyclisation of 2-substituted ethynylmalonates as a key starting material are described. Within this study, we were able to show that the 3-iodo-1 H-indene can be used as a synthetic platform not only for the palladium chemistry but also as a catalyst for the in situ generation of [text unavailable] hypervalent iodine reagent. Additionally, 3-iodo-1 H-indene derivatives have the potential to perform asymmetric synthesis. Third chapter demonstrates tandem iodine mediated carboannulation of the stilbene malonate derivatives via either 5-exo- or 6-endo-trig mode under basic reagents with subsequent lactonisation to structurally complex indanes and tetrahydronaphthalenes with three new stereogenic centres. In the present study, a unique stereochemistry was observed in the case of tetrahydroindenofuranones and confirmed by single crystal X-ray analysis. These cyclisations proceed exclusively with the retention of configuration to form tetrahydroindenofuranones. Both the compounds formed as a single diastereomers as judged from their 1H and 13C NMR spectrum. In fourth chapter the synthesis of novel simplified analogues of IBA by oxidation of [text unavailable] diiodoacrylic acids are described. Additionally, the ligand exchange resulted in tosylate derivative. The new reagents have been utilized in various well established oxidative transformations with superior or similar reactivity as conventional hypervalent iodine(III) reagents.
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Jia, Zhiyu. "Transformations promoted by the hypervalent iodine reagents." Doctoral thesis, Universitat Autònoma de Barcelona, 2014. http://hdl.handle.net/10803/134832.

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Malmedy, Florence. "Stereoselective transformations using chiral hypervalent iodine reagents." Thesis, Cardiff University, 2016. http://orca.cf.ac.uk/93576/.

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Hypervalent iodine (III) compounds are efficient, selective and environmentally friendly reagents. Due to their electrophilic nature and excellent leaving group ability, they can be used to mediate oxidative transformations; for example, the oxidation of sulfides to sulfoxides, the α-functionalisation of ketones, the dearomatisation of phenols, the functionalisation of alkenes and, more recently, the rearrangement of various substrates. In this thesis, the stereoselective rearrangement of propiophenone derivatives mediated by chiral hypervalent iodine reagents is described (Scheme i). A chiral lactate-based iodine (III) reagent was used to synthesise 2-arylpropionate derivatives with moderate to good yields and enantioselectivities. These compounds are highly attractive as they are direct precursors to Non-Steroidal Anti Inflammatory Drugs (NSAIDs). Scheme i. Rearrangement of propiophenone derivatives to 2-aryl-propionates. The cyclisation of malonate derivatives, mediated by hypervalent iodine reagents has also been investigated (Scheme ii). Several lactone derivatives were synthesised with this method, achieving moderate to good yields. Scheme ii. Cyclisation of malonate derivatives to synthesise functionalised lactones. Finally, the design of a new hypervalent iodine reagent is described (Figure i). After its synthesis, the pyridine-based reagent was tested in several model reactions, usually mediated by iodine (III) reagents. Its reactivity was similar to the one of other hypervalent iodine reagents. However, its ability to induce stereoselectivity to different products was quite poor. Figure i. Structure of the new hypervalent iodine reagent.
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Edmunds, J. J. "Novel fluorination reactions via hypervalent iodine reagents." Thesis, Imperial College London, 1988. http://hdl.handle.net/10044/1/47045.

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Gurung, Ras Kumari. "INVESTIGATIONS OF HYPERVALENT IODINE COMPOUNDS IN ORGANIC TRANSFORMATIONS." OpenSIUC, 2015. https://opensiuc.lib.siu.edu/dissertations/991.

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The main aim of the work presented here is to develop new, practical, economical, and environmental friendly synthetic protocols for various organic transformations with hypervalent iodine compounds, which have attracted explosive interest among chemistry communities because of their versatility and mildness in inducing many organic transformations. Chapter 1 briefly introduces the history of hypervalent iodine compounds, nomenclature, classification, bonding and reactivity patterns. The preparation and practical applications of typical I(III) and I(V) compounds have also been briefly surveyed. Chapter 2 provides details on hypervalent iodine compounds catalyzed oxidation of benzylic C-H to the corresponding carbonyl compounds with Oxone. The catalytic efficiency is influenced by the rate of in situ generation of catalyst with Oxone and their stability. The effectiveness in situ generated 35', 50' and 51' are almost the same, leading to low to moderate yields of products, while 18 and 47' give moderate to high yields. Compound 48' was founds to be the most active catalyst in this study. A possible mechanism is also proposed. Chapter 3 covers a surprising reaction between IBX or IBA and alkyl halides promoted by quaternary ammonium halides. In the absence of quaternary ammonium halides, no reaction occurred between IBX or IBA and alkyl halides. However, in the presence of quaternary ammonium halides, IBX or IBA and alkyl halides react smoothly to form the corresponding alkyl iodobenzoates. When IBX or IBA is treated with a quaternary ammonium halide, it will decompose to 2-iodobenzoic acid. The presence of a nucleophilic halide ion is essential for such reaction to occur. Replacing halides with non-nucleophilic BF4- halts the reaction. Benzylic halides provides a better yield than aliphatic alkyl halide. Thus, it is believed that there is a fast interaction between the nucleophilic halides and electrophilic iodine in IBX or IBA. A plausible reaction mechanism is proposed. Chapter 4 details our research on the oxidative cleavage of C=C with PIFA/water. In the presence of a small amount of water in acetonitrile at 65-70 oC, [bis(trifluoroacetoxy)iodo]benzene (PIFA, 26) converts styrenes into benzaldehydes in good to high yields. Contrary to literature description that electron-rich styrenes primarily produces phenylacetaldehydes as major products through a 1, 2-phenyl migration, we have found that these styrenes can be converted to benzaldehydes in high yields. It was found that three equiv of 26 and one equiv of water were necessary to achieve high yields. Two pathways were believed responsible for the high yield of benzaldehydes: (1) cleavage of the glycol intermediates; (2) further oxidative cleavage of the 1, 2-phenyl migration product - phenylacetaldehydes. Chapter 5 describes a preliminary investigation on perfluoroalkylation reaction of styrene with [bis(trifluoroacetoxy)iodo]butane (32). p-t-Butylstyrene reacts with 32 in the presence of water produced moderate yields of hydroxyperfluorinated product, 1-(4-tert-butyl-phenyl)-3,3,4,4,5,5,6,6,6-nonafluoro-hexan-1-ol (73), along with 1-(4-tert-butyl- phenyl)-2-iodo-ethanol (72) and 1-(4-tert-butyl-phenyl)-ethane-1,2-diol (74). Electrophilic addition of 32 on the C=C bond, hydration of the intermediate, and reductive elimination were believed to have been involved. Chapter 6 summarizes all of the work carried out in the previous chapters and provides some insight into future studies.
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Romero, Segura Rafael Martín. "Development of hypervalent iodine(iii)-mediated chemical reactions." Doctoral thesis, Universitat Rovira i Virgili, 2017. http://hdl.handle.net/10803/402470.

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El iode hipervalent representa una poderosa eina per dur a terme diferent reaccions d’oxidació en condicions lliures de metalls. S’han realitzat estudis mecanístics que inclouen experiments de control físic-orgànics relatius a la diaminació intermolecular d’alquens mediats per iode(III) que han servit per a demostrar la veracitat dels càlculs computacionals realitzats prèviament. Aquesta informació va proporcionar una visió crucial per al desenvolupament d’una nova reacció enantioselectiva de diaminació d’estirens catalitzada per iode(III). El disseny d’un nou catalitzador quiral de iode basat en l’ús de l’àcid làctic com a font econòmica de quiralitat representa la clau d’aquest assoliment. L’optimització del catalitzador implica l’increment de la densitat d’electrònica en el nucli de iode i un motiu d’amida secundària en la cadena lateral de lactat quiral. Entre els diferents oxidants terminals, el mCPBA ha resultat ser el més eficient conduint a bons rendiments i excel·lent enantioselectivitats (>99% ee). L’abast de la reacció comprèn alquens terminals i alquens interns dins del motiu de l’estirè. En un estudi addicional, es va aconseguir la formació d’un nou enllaç carboni-bor. Així doncs, la borilació de sals de diariliodoni va ser possible després d’identificar el contra-anió del reactiu de diariliodoni més adequat. Mitjançant la generació in situ umpolung al centre de bor, la seva arilació per el reactiu hipervalent esdevé possible. Amb aquest fi, diferent acetats de diariliodoni van ser sintetitzats, demostrant la gran aplicabilitat d’aquest nou mètode respecte al grup aromàtic transferible. Aquest mètode s’afegeix a l’escàs nombre de reaccions de borilació en condicions lliures de metalls.
Los reactivos de iodo hipervalente representan una herramienta muy poderosa para la realización de diferentes oxidaciones libres de metal. Se llevaron a cabo estudios mecanísticos incluyendo experimentos físico-orgánicos de control respecto a la diaminación intermolecular de alquenos, demostrando la veracidad de los cálculos DFT previamente realizados. Esta información resultó crucial para el desarrollo de una pionera diaminación enantioselectiva de estirenos catalizada por iodo(III). Uno de los mayores logros es el diseño de un nuevo catalizador de iodo quiral basado en el ácido láctico como fuente económica de información estereoquímica. La optimización del catalizador incluye un aumento crucial de electrondensidad en el núcleo de iodo y la presencia del grupo amida en la cadena de lactato quiral. Entre los diferentes oxidantes terminales probados, mCPBA resultó ser el más eficiente, dando buenos rendimientos y una enantioselectividad sin precedentes, siendo ésta siempre superior al 90% ee. Esta reacción puede extenderse a alquenos terminales e internos que contengan la estructura de estireno. Este logro representa uno de los resultados más avanzados en la diaminación asimétrica de alquenos. En un estudio adicional, se consiguió una nueva formación de enlaces carbono-boro. Aquí, la borilación de sales de diariliodonio fue posible tras la identificación de un contraión apropiado en el reactivo de diariliodonio. Gracias a la generación in situ de un umpolung en el centro de boro, su arilación por el reactivo hipervalente es posible. Con esta finalidad, se sintetizaron diferentes acetatos de diariliodonio y se demostró la gran aplicabilidad de esta metodología en la transferencia de grupos aromáticos. Este protocolo representa uno de los pocos procesos económicos de borilación en ausencia de metal.
Hypervalent iodine(III) reagents represent a powerful tool for the realisation of different metal-free oxidation reactions. Mechanistic studies including physical-organic control experiments concerning the oxidative iodine(III)-mediated intermolecular diamination of alkens were carried out, demonstrating the veracity of previous DFT calculations. This information provided crucial insight for the development of a pioneering iodine(III)-catalysed enantioselective diamination of styrenes. The design of a novel chiral iodine catalyst based on lactic acid as economic chiral information source represents the key accomplishment. Catalyst optimisation involves a crucial electrondensity enhancement at the iodine core and a secondary amide motive in the chiral lactate side chain. Among different terminal oxidants, conventional mCPBA emerged as the most efficient one leading to good yields and unprecedented enantioselectivities of above 90% ee. The scope of the reaction comprises terminal and internal alkenes within the styrene motif. It represents the state of the art in asymmetric diamination of alkenes. In an additional study, a novel carbon-boron bond formation was accomplished. Here, borylation of diaryliodonium salts was encountered feasible upon identification of a suitable counterion in the diaryliodonium reagent. By generating an in situ umpolung at the boron centre, its arylation by the hypervalent reagent becomes viable. To this end, different diaryliodonium acetates were synthesised, thereby successfully demonstrating a broad applicability of this new methodology regarding the transferable aromatic group. This protocol adds to the still scarce number of economic borylation reactions under metal-free conditions.
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Page, Thomas Keri. "Synthesis and reactivity of chiral hypervalent iodine compounds." Thesis, Cardiff University, 2009. http://orca.cf.ac.uk/54874/.

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Hypervalent iodine compounds are molecules of increasing interest to the synthetic chemist. Their low toxicity when compared to heavy metal reagents and their ease of use in the laboratory are helping to establish them into the armoury of the synthetic chemist. More recently, research into chiral hypervalent iodine compounds has been the main focus. The work performed during this research tenure is based upon the development of new chiral hypervalent iodine reagents for use in stereoselective synthesis and this research can be summarised into three main sections: Synthesis of novel chiral iodine(III) compounds; Reactivity of chiral iodine(III) compounds; Novel oxididative procedure. The synthesis of new chiral iodine(III) compounds and their use in asymmetric oxidative functionalisations are described herein. The use of stoichiometric quantities of these iodine(III) reagents with 1 eq of pTsOHO in the a-oxytosylation of ketones and 2 eq of /7TSOH H2 O in the dioxytosylation of alkenes, have given the corresponding products in good yields, 57-76% (3-12% ee) and 48-75% (9-16% ee) respectively. Additionally, a new catalytic method is described in which the presence of a stoichiometric oxidant, 1 eq of /7TSOH H2O and only catalytic quantities of the chiral iodine(I) reagent is necessary to afford a-oxytosylated ketones. The final aspect of the research has dealt with the problems associated with oxidizing iodine(I) compounds to iodine(III) compounds. The development of a new method to oxidise iodine(I) compounds to bis(trifluoroacetoxy)iodo arenes through the use of urea-hydrogen peroxide adduct and trifluoroacetic anhydride is also described.
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Jegasothy, Shankar. "Kinetic studies on polymer-supported hypervalent iodine oxidants." Thesis, University of Cambridge, 2005. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.615044.

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Wu, Yichen. "Hypervalent Iodine as Directing Tool in Iodine-Retentive Transformation of C-H Bonds." Doctoral thesis, Universitat Rovira i Virgili, 2017. http://hdl.handle.net/10803/461093.

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La química del iode hipervalente és una potent i versàtil eina en síntesi orgànica. En particular, els compostos orgànics de iode (III) s'han utilitzat com a oxidants de 2 electrons, així com agents de transferència de grups en diversos processos oxidatius de funcionalització. Al marge d'un nombre reduït de casos especials, aquestes transformacions van acompanyades per la pèrdua del fragment corresponent a una molècula de iodoarè. Una opció menys explorada, però sintèticament atractiva, consisteix en la incorporació tant del grup orgànic com de l'àtom de iode en el producte final. Aquest enfocament presenta un clar interès sintètic atès que la retenció de l'àtom de iode possibilita la posterior derivatització. Al llarg d'aquesta Memòria es mostren diferents reaccions d'acoblament dirigides per iode partint de compostos de iode trivalent com a substrats. En primer lloc, es descriu un nou mètode de α-arilació directa de cetones en absència de metalls. La transferència del grup aril té lloc via acoblament orto al iode, i es basa en l'activació in situ d’aquest àtom. El nou procediment presenta bona tolerància als diferents grups funcionals del areno. La selectivitat orto es va relacionar, mitjançant càlculs DFT, amb un procés de reordanament iodonio-Claisen amb una barrera d’activació inusualment baixa. S'ha desenvolupat també un nou tipus de reaccions de benzilació regioselectiva de l'anell aromàtic a partir de derivats Ar(OAc)2 i bencil(trimetil)silà. Cal destacar que aquest procés l'acoblament carboni-carboni té lloc selectivament en la posició para respecte de l'àtom de iode. Per últim, es presenta una nova estratègia per a un procés de "iodoarilació" oxidant de l’anell imidazolic. Aquest procediment es basa en l'activació de l'enllaç NH de l'imidazol amb ArI(OAc) 2, seguida per una transferència 1,3 I-a-N del grup que dona lloc a l'obtenció de N1-aril-5-yodoimidazoles. L'impacte sintètic de la transformació emana de la inherent capacitat dels N1-aril-5-iodoimidazols d'actuar com a precursors per a diversos derivats 1,5-substituïts d'imidazol.
La química del yodo hipervalente es una potente y versátil herramienta en síntesis orgánica. En particular, los compuestos orgánicos de yodo(III) se han utilizado como oxidantes de 2 electrones, así como agentes de transferencia de grupos en diversos procesos oxidantes de funcionalización. Salvo unas pocas excepciones, estas transformaciones van acompañadas por la pérdida del fragmento yodobenceno. Una opción menos explorada, pero sintéticamente atractiva, consiste en la incorporación tanto del grupo orgánico como del átomo de yodo en el producto final. Este enfoque presenta un claro interés sintético dado que la retención del átomo de yodo posibilita su posterior derivatización. A lo largo de esta Memoria se muestran distintas reacciones de acoplamiento dirigidas por el yodo partiendo de compuestos de yodo trivalente como sustratos. En primer lugar, se describe un nuevo método de α-arilación directa de cetonas en ausencia de metales. La transferencia del grupo arilo tiene lugar vía acoplamiento orto al yodo, y se basa en la activación in situ del átomo de yodo. Este procedimiento presenta buena tolerancia a los distintos grupos funcionales del areno. La selectividad orto se relacionó, mediante cálculos DFT, con un mecanismo de reorganización yodonio-Claisen con una barrera de activación inusualmente baja. Se ha desarrollado también una nueva vía de acceso para reacciones de bencilación regioselectiva del anillo aromático del ArI(OAc)2 con benciltrimetilsilano. Es interesante destacar que este proceso el acoplamiento carbono-carbono tiene lugar selectivamente en la posición para respecto del átomo de yodo. En último lugar, se presenta una nueva estrategia para la “yodoarilación” oxidante de imidazoles. Este procedimiento se basa en la activación del anillo NH-imidazólico con ArI(OAc)2, seguida por una transferencia 1,3 I-a-N del grupo arilo para la obtención de N1-aril-5-yodoimidazoles. El impacto sintético de la transformación emana de la inherente capacidad de los N1-arilo-5-iodo-imidazoles de actuar como precursores para diversos derivados 1,5-sustituidos de imidazol.
The chemistry of organic hypervalent iodine compounds has been a potent and versatile toolbox in organic synthesis. In particular, organic λ3-iodanes have been utilized as terminal 2-electron oxidants, as well as group transfer agents in a wide range oxidative functionalization processes. With few exceptions, such transformations are accompanied by the liberation of the parent organoiodine fragment. A less explored, but synthetically attractive possibility consists in incorporating both the organic group and the iodine atom into the final product. Such approach presents a clear synthetic appeal, given that the iodine retention opens the door for downstream derivatization. This thesis describes a series of such “iodine-directed” coupling reaction employing organo-λ3-iodanes as substrates. In one approach, a new method for direct metal-free α-arylation of ketones is described. The aryl transfer takes place via the coupling ortho to iodine, and is based on in situ hypervalent activation of the iodine atom. The protocol shows good functional group compatibility on the arene core. The ortho-selectivity was rationalized by DFT calculations through an unusual low-barrier “iodonio-Claisen¨ process. We also developed a new approach for regioselective benzylation of the ArI(OAc)2 cores using benzyltrimethylsilane. Interestingly, the carbon-carbon coupling now takes place selectively at para position to the iodine atom. Finally, an approach for oxidative “iodoarylation” of imidazoles was uncovered. The procedure relies on an efficient activation of the parent NH-imidazole with ArI(OAc)2, followed by copper-catalyzed intramolecular 1,3 I-to-N aryl transfer to constitute the synthetically challenging N1-aryl-5-iodoimidazoles. The importance of this manifold resides in the ability of the 5-iodoimidazoles to act as precursors for a range of 1,5-substituted imidazoles.
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10

Jain, Nikita. "Chiral hypervalent iodine mediated enantioselective oxidative dearomatization of naphthols." Thesis, University of British Columbia, 2017. http://hdl.handle.net/2429/62521.

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This dissertation investigates and describes the hypervalent iodine mediated dearomatization of naphthols, thereby yielding diversity of spiro-heterocyclic compounds in both racemic and chiral form. The first part of this thesis discloses the synthesis of racemic spiropyrrolidines and spirolactams via oxidative amidation of corresponding naphtholic sulfonamides, employing DIB as the oxidant. Enantioselective variant of the same have been demonstrated by using in situ generated chiral hypervalent iodine to provide chiral spiropyrrolidines. A noteworthy side reaction discovered in the course of these studies is the asymmetric oxidative addition of meta-chlorobenzoic acid to the naphtholic sulfonamides. The resulting acyloxylated adducts were formed with a greater degree of asymmetric induction compared to spiropyrrolidines in the same reaction mixture. Based on the results obtained from optimization study and substrate scope, plausible mechanistic insights of both cyclization and acyloxylation reactions have been provided. The second part of this thesis unravels the spiroetherification of naphtholic alcohols, thereby yielding spiroethers both in racemic and chiral form. Chiral hypervalent iodine reagents generated in situ provided a range of spiroethers with excellent ee’s and high yields. These chiral oxidants have been evaluated for kinetic resolution of naphtholic primary alcohols bearing stereogenic center at β-position in the side chain.
Science, Faculty of
Chemistry, Department of
Graduate
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Books on the topic "Hypervalent iodine"

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Zhdankin, Viktor V. Hypervalent Iodine Chemistry. Chichester, UK: John Wiley & Sons Ltd, 2013. http://dx.doi.org/10.1002/9781118341155.

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Wirth, Thomas, ed. Hypervalent Iodine Chemistry. Cham: Springer International Publishing, 2016. http://dx.doi.org/10.1007/978-3-319-33733-3.

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Wirth, Thomas, ed. Hypervalent Iodine Chemistry. Berlin, Heidelberg: Springer Berlin Heidelberg, 2002. http://dx.doi.org/10.1007/3-540-46114-0.

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Andrews, Ian Philip. Hypervalent iodine oxidations of substituted pyridines. Norwich: University of East Anglia, 1992.

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McLaren, Lee. Synthetic applications of hypervalent iodine reagents: Total synthesis of aranorosin. Norwich: Universityof East Anglia, 1994.

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Koyuncu, Demet. Functional group oxidations using sodium perborate and hypervalent iodine reagents. Norwich: Universityof East Anglia, 1992.

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Wirth, Thomas. Hypervalent Iodine Chemistry. Springer, 2016.

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Wirth, Thomas. Hypervalent Iodine Chemistry. Springer International Publishing AG, 2018.

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Wirth, Thomas. Hypervalent Iodine Chemistry. Springer London, Limited, 2016.

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Katritzky, Alan R., O. Meth-Cohn, A. Varvoglis, and C. S. Rees. Hypervalent Iodine in Organic Synthesis. Elsevier Science & Technology Books, 1996.

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Book chapters on the topic "Hypervalent iodine"

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Dohi, Toshifumi, and Yasuyuki Kita. "Hypervalent Iodine." In Iodine Chemistry and Applications, 103–57. Hoboken, NJ: John Wiley & Sons, Inc, 2014. http://dx.doi.org/10.1002/9781118909911.ch7.

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Kumar, Ravi, and Thomas Wirth. "Asymmetric Synthesis with Hypervalent Iodine Reagents." In Hypervalent Iodine Chemistry, 243–61. Cham: Springer International Publishing, 2015. http://dx.doi.org/10.1007/128_2015_639.

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Murarka, Sandip, and Andrey P. Antonchick. "Oxidative Heterocycle Formation Using Hypervalent Iodine(III) Reagents." In Hypervalent Iodine Chemistry, 75–104. Cham: Springer International Publishing, 2015. http://dx.doi.org/10.1007/128_2015_647.

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Maertens, Gaëtan, and Sylvain Canesi. "Rearrangements Induced by Hypervalent Iodine." In Hypervalent Iodine Chemistry, 223–41. Cham: Springer International Publishing, 2015. http://dx.doi.org/10.1007/128_2015_657.

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Früh, Natalja, Julie Charpentier, and Antonio Togni. "Iodanes as Trifluoromethylation Reagents." In Hypervalent Iodine Chemistry, 167–86. Cham: Springer International Publishing, 2015. http://dx.doi.org/10.1007/128_2015_658.

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Waser, Jerome. "Alkynylation with Hypervalent Iodine Reagents." In Hypervalent Iodine Chemistry, 187–222. Cham: Springer International Publishing, 2015. http://dx.doi.org/10.1007/128_2015_660.

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Olofsson, Berit. "Arylation with Diaryliodonium Salts." In Hypervalent Iodine Chemistry, 135–66. Cham: Springer International Publishing, 2015. http://dx.doi.org/10.1007/128_2015_661.

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Muñiz, Kilian. "Aminations with Hypervalent Iodine." In Hypervalent Iodine Chemistry, 105–33. Cham: Springer International Publishing, 2015. http://dx.doi.org/10.1007/128_2015_663.

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Protasiewicz, John D. "Organoiodine(III) Reagents as Active Participants and Ligands in Transition Metal-Catalyzed Reactions: Iodosylarenes and (Imino)iodoarenes." In Hypervalent Iodine Chemistry, 263–88. Cham: Springer International Publishing, 2015. http://dx.doi.org/10.1007/128_2015_664.

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Quideau, Stéphane, Laurent Pouységu, Philippe A. Peixoto, and Denis Deffieux. "Phenol Dearomatization with Hypervalent Iodine Reagents." In Hypervalent Iodine Chemistry, 25–74. Cham: Springer International Publishing, 2016. http://dx.doi.org/10.1007/128_2015_665.

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Conference papers on the topic "Hypervalent iodine"

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Moriarty, Robert M., Jaffar S. Khosrowshahi, and Tomasz Dalecki. "Hypervalent Iodine Iodinative Decarboxylation Of Cubyl And Homocubyl Carboxylic Acids." In 1988 Los Angeles Symposium--O-E/LASE '88, edited by Joseph Flanagan. SPIE, 1988. http://dx.doi.org/10.1117/12.943749.

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Utaka, Aline, Lívia N. Cavalcanti, and Luiz F. Silva Jr. "Electrophilic alkynylation of ketones using hypervalent iodine reagent: a new approach to quaternary carbon formation." In 15th Brazilian Meeting on Organic Synthesis. São Paulo: Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-15bmos-bmos2013_201391510568.

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Dávila Rodríguez, Izaskun. "Searching for new applications of the hypervalent iodine reagents in the construction of nitrogen containing compounds." In MOL2NET 2016, International Conference on Multidisciplinary Sciences, 2nd edition. Basel, Switzerland: MDPI, 2016. http://dx.doi.org/10.3390/mol2net-02-h007.

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