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Journal articles on the topic 'Iodure hypervalent'

Author: Grafiati

Published: 19 October 2024

Last updated: 31 July 2025

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1

Kiyokawa, Kensuke, and Satoshi Minakata. "Iodine-Based Reagents in Oxidative Amination and Oxygenation." Synlett 31, no. 09 (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 Decar

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2

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 bondi

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3

Kuhn, Norbert, Qutaiba Abu-Salem, Torben Gädt, Steffi Reit, and Manfred Steimann. "Trimethyl(4-Iodophenyl)Ammoniumiodid, Eine Hypervalente Verbindung Des Iods." Zeitschrift für Naturforschung B 62, no. 6 (2007): 871–72. http://dx.doi.org/10.1515/znb-2007-0619.

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4

Goesten, Maarten G., Roald Hoffmann, F. Matthias Bickelhaupt, and Emiel J. M. Hensen. "Eight-coordinate fluoride in a silicate double-four-ring." Proceedings of the National Academy of Sciences 114, no. 5 (2017): 828–33. http://dx.doi.org/10.1073/pnas.1615742114.

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Fluoride, nature’s smallest anion, is capable of covalently coordinating to eight silicon atoms. The setting is a simple and common motif in zeolite chemistry: the box-shaped silicate double-four-ring (D4R). Fluoride seeks its center. It is the strain of box deformation that keeps fluoride in the middle of the box, and freezes what would be a transition state in its absence. Hypervalent bonding ensues. Fluoride’s compactness works to its advantage in stabilizing the cage; chloride, bromide, and iodide do not bring about stabilization due to greater steric repulsion with the box frame. The comb

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5

LaMartina, Kelsey B., Haley K. Kuck, Linda S. Oglesbee, Asma Al-Odaini, and Nicholas C. Boaz. "Selective benzylic C–H monooxygenation mediated by iodine oxides." Beilstein Journal of Organic Chemistry 15 (March 5, 2019): 602–9. http://dx.doi.org/10.3762/bjoc.15.55.

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A method for the selective monooxdiation of secondary benzylic C–H bonds is described using an N-oxyl catalyst and a hypervalent iodine species as a terminal oxidant. Combinations of ammonium iodate and catalytic N-hydroxyphthalimide (NHPI) were shown to be effective in the selective oxidation of n-butylbenzene directly to 1-phenylbutyl acetate in high yield (86%). This method shows moderate substrate tolerance in the oxygenation of substrates containing secondary benzylic C–H bonds, yielding the corresponding benzylic acetates in good to moderate yield. Tertiary benzylic C–H bonds were shown

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6

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 intermediate

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7

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 (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 Hypervale

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8

Maegawa, Tomohiro, Yasuyoshi Miki, Ryohei Oishi, Kazutoshi Segi, Hiromi Hamamoto, and Akira Nakamura. "Hypervalent Iodine-Mediated Beckmann Rearrangement of Ketoximes." Synlett 29, no. 11 (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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9

Xing, Linlin, Yong Zhang, and Yunfei Du. "Hypervalent Iodine-Mediated Synthesis of Spiroheterocycles via Oxidative Cyclization." Current Organic Chemistry 23, no. 1 (2019): 14–37. http://dx.doi.org/10.2174/1385272822666181211122802.

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Hypervalent iodine reagents have been widely used in the construction of many important building blocks and privileged scaffolds of bioactive natural products. This review article aims to briefly discuss strategies that have used hypervalent iodine reagents as oxidants to synthesize spiroheterocyclic compounds and to stimulate further study for novel syntheses of spiroheterocyclic core structures using hypervalent iodine reagents under metal-free conditions.

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10

Mowdawalla, Cyrus, Faiz Ahmed, Tian Li, et al. "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 activat

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11

Singh, Fateh V., Priyanka B. Kole, Saeesh R. Mangaonkar, and Samata E. Shetgaonkar. "Synthesis of spirocyclic scaffolds using hypervalent iodine reagents." Beilstein Journal of Organic Chemistry 14 (July 17, 2018): 1778–805. http://dx.doi.org/10.3762/bjoc.14.152.

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Hypervalent iodine reagents have been developed as highly valuable reagents in synthetic organic chemistry during the past few decades. These reagents have been identified as key replacements of various toxic heavy metals in organic synthesis. Various synthetically and biologically important scaffolds have been developed using hypervalent iodine reagents either in stoichiometric or catalytic amounts. In addition, hypervalent iodine reagents have been employed for the synthesis of spirocyclic scaffolds via dearomatization processes. In this review, various approaches for the synthesis of spiroc

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12

Hyatt, I. F. Dempsey, Loma Dave, Navindra David, Kirandeep Kaur, Marly Medard, and Cyrus Mowdawalla. "Hypervalent iodine reactions utilized in carbon–carbon bond formations." Organic & Biomolecular Chemistry 17, no. 34 (2019): 7822–48. http://dx.doi.org/10.1039/c9ob01267b.

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13

Li, Xiaoxian, Tongxing Liu, Beibei Zhang, et al. "Formation of Carbon-Carbon Bonds Mediated by Hypervalent Iodine Reagents Under Metal-free Conditions." Current Organic Chemistry 24, no. 1 (2020): 74–103. http://dx.doi.org/10.2174/1385272824666200211093103.

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During the past several decades, hypervalent iodine reagents have been widely used in various organic transformations. Specifically, these exclusive classes of reagents have been extensively used for the construction of carbon-carbon bonds. This review aims to cover all the reactions involving the construction of carbon-carbon bonds mediated by hypervalent iodine reagents, providing references and highlights for synthetic chemists who are interested in hypervalent iodine chemistry.

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14

Sun, Tian-Yu, Kai Chen, Qihui Lin, Tingting You, and Penggang Yin. "Predicting the right mechanism for hypervalent iodine reagents by applying two types of hypervalent twist models: apical twist and equatorial twist." Physical Chemistry Chemical Physics 23, no. 11 (2021): 6758–62. http://dx.doi.org/10.1039/d0cp06692c.

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Since hypervalent twist followed by reductive elimination is a general reaction pattern for hypervalent iodine reagents, mechanistic studies about the hypervalent twist step could provide significant guidance for experiments.

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15

Kalek, Marcin, Manoj Ghosh, and Adam Rajkiewicz. "Organocatalytic Group Transfer Reactions with Hypervalent Iodine Reagents." Synthesis 51, no. 02 (2018): 359–70. http://dx.doi.org/10.1055/s-0037-1609639.

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In recent years, a plethora of synthetic methods that employ hypervalent iodine compounds donating an atom or a group of atoms to an acceptor molecule have been developed. Several of these transformations utilize organocatalysis, which complements well the economic and environmental advantages offered by iodine reagents. This short review provides a systematic survey of the organocatalytic approaches that have been used to promote group transfer from hypervalent iodine species. It covers both the reactions in which an organocatalyst is applied to activate the acceptor, as well as those that ex

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16

Kupwade, Ravindra V. "A Concise Review of Hypervalent Iodine with Special Reference to Dess- Martin Periodinane." Mini-Reviews in Organic Chemistry 17, no. 8 (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

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17

Maegawa, Tomohiro, Ayako Shibata, Sara Kitamoto, et al. "Dehydroxymethyl Bromination of Alkoxybenzyl Alcohols by Using a Hypervalent Iodine Reagent and Lithium Bromide." Synlett 29, no. 17 (2018): 2275–78. http://dx.doi.org/10.1055/s-0037-1610980.

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We describe the dehydroxymethylbromination of alkoxybenzyl alcohol by using a hypervalent iodine reagent and lithium bromide in F3CCH2OH at room temperature. Selective monobromination or dibromination was possible by adjusting the molar ratios of hypervalent iodine reagent and lithium bromide.

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18

Li, Xiang, Pinhong Chen, and Guosheng Liu. "Recent advances in hypervalent iodine(III)-catalyzed functionalization of alkenes." Beilstein Journal of Organic Chemistry 14 (July 18, 2018): 1813–25. http://dx.doi.org/10.3762/bjoc.14.154.

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Hypervalent iodine(III) reagents have been well-developed and widely utilized in functionalization of alkenes, however, generally either stoichiometric amounts of iodine(III) reagents are required or stoichiometric oxidants such as mCPBA are employed to in situ generate iodine(III) species. In this review, recent developments of hypervalent iodine(III)-catalyzed functionalization of alkenes and asymmetric reactions using a chiral iodoarene are summarized.

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19

Yoshimura, Yuichi, Hideaki Wakamatsu, Yoshihiro Natori, Yukako Saito, and Noriaki Minakawa. "Glycosylation reactions mediated by hypervalent iodine: application to the synthesis of nucleosides and carbohydrates." Beilstein Journal of Organic Chemistry 14 (June 28, 2018): 1595–618. http://dx.doi.org/10.3762/bjoc.14.137.

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To synthesize nucleoside and oligosaccharide derivatives, we often use a glycosylation reaction to form a glycoside bond. Coupling reactions between a nucleobase and a sugar donor in the former case, and the reaction between an acceptor and a sugar donor of in the latter are carried out in the presence of an appropriate activator. As an activator of the glycosylation, a combination of a Lewis acid catalyst and a hypervalent iodine was developed for synthesizing 4’-thionucleosides, which could be applied for the synthesis of 4’-selenonucleosides as well. The extension of hypervalent iodine-medi

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20

Liu, Jialin, Xiaoyu Xiong, Jie Chen, Yuntao Wang, Ranran Zhu, and Jianhui Huang. "Double C–H Activation for the C–C bond Formation Reactions." Current Organic Synthesis 15, no. 7 (2018): 882–903. http://dx.doi.org/10.2174/1570179415666180720111422.

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Background: Among the numerous bond-forming patterns, C–C bond formation is one of the most useful tools for building molecules for the chemical industry as well as life sciences. Recently, one of the most challenging topics is the study of the direct coupling reactions via multiple C–H bond cleavage/activation processes. A number of excellent reviews on modern C–H direct functionalization have been reported by Bergman, Bercaw, Yu and others in recent years. Among the large number of available methodologies, Pdcatalyzed reactions and hypervalent iodine reagent mediated reactions represent the

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21

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 (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 summa

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22

OM, PRAKASH, SAINI NEENA, and KUMAR SHARMA PAWAN. "Hypervalent Iodine in Organic Synthesis : Convenient and General Procedures for a-Functionalisation of Ketones." Journal of Indian Chemical Society Vol. 72, Feb 1995 (1995): 129–31. https://doi.org/10.5281/zenodo.5901157.

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Department of Chemistry, Kurukshetra University. Kurukshetra-132 119 <em>Manuscript received 28 April 1993, accepted 19 October 1993</em> Hypervalent Iodine in Organic Synthesis : Convenient and General Procedures for α-Functionalisation of Ketones

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23

Kotali, Antigoni. "Hypervalent Iodine." Molecules 10, no. 1 (2005): 181–82. http://dx.doi.org/10.3390/10010181.

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24

Krylov, Igor B., Stanislav A. Paveliev, Mikhail A. Syroeshkin, et al. "Hypervalent iodine compounds for anti-Markovnikov-type iodo-oxyimidation of vinylarenes." Beilstein Journal of Organic Chemistry 14 (August 16, 2018): 2146–55. http://dx.doi.org/10.3762/bjoc.14.188.

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The iodo-oxyimidation of styrenes with the N-hydroxyimide/I2/hypervalent iodine oxidant system was proposed. Among the examined hypervalent iodine oxidants (PIDA, PIFA, IBX, DMP) PhI(OAc)2 proved to be the most effective; yields of iodo-oxyimides are 34–91%. A plausible reaction pathway includes the addition of an imide-N-oxyl radical to the double C=C bond and trapping of the resultant benzylic radical by iodine. It was shown that the iodine atom in the prepared iodo-oxyimides can be substituted by various nucleophiles.

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25

Zheng, Hanliang, and Xiao-Song Xue. "Recent Computational Studies on Mechanisms of Hypervalent Iodine(III)-Promoted Dearomatization of Phenols." Current Organic Chemistry 24, no. 18 (2020): 2106–17. http://dx.doi.org/10.2174/1385272824999200620223218.

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Hypervalent iodine-promoted dearomatization of phenols has received intense attention. This mini-review summarizes recent computational mechanistic studies of phenolic dearomatizations promoted by hypervalent iodine(III) reagents or catalysts. The first part of this review describes mechanisms of racemic dearomatization of phenols, paying special attention to the associative and dissociative pathways. The second part focuses on mechanisms and selectivities of diastereo- or enantio-selective dearomatization of phenols.

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26

Fujita, Morifumi, Koki Miura, and Takashi Sugimura. "Enantioselective dioxytosylation of styrenes using lactate-based chiral hypervalent iodine(III)." Beilstein Journal of Organic Chemistry 14 (March 20, 2018): 659–63. http://dx.doi.org/10.3762/bjoc.14.53.

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A series of optically active hypervalent iodine(III) reagents prepared from the corresponding (R)-2-(2-iodophenoxy)propanoate derivative was employed for the asymmetric dioxytosylation of styrene and its derivatives. The electrophilic addition of the hypervalent iodine(III) compound toward styrene proceeded with high enantioface selectivity to give 1-aryl-1,2-di(tosyloxy)ethane with an enantiomeric excess of 70–96% of the (S)-isomer.

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27

Dohi, Toshifumi. "Recent Topics in Iodine Reagents and Compounds in Organic Chemistry." Current Organic Chemistry 26, no. 21 (2022): 1915–16. http://dx.doi.org/10.2174/138527282621230123155131.

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This Special Issue would cover the hot topics on recent synthetic interest in iodine reagents and related chemistry as well as the unique characteristics of hypervalent iodine compounds. The excellent reviews by the experts and eminent researchers engaged in the recent advances, i.e., preparations, reactions, and mechanistic studies of hypervalent iodine compounds, and their utilizations as reagents and organocatalysts in controlled reactions for synthesizing useful organic molecules, such as pharmaceutical compounds and organic materials, are provided in this Special Issue.

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28

Sokolovs, Igors, Edgars Suna та Robert Francke. "(Invited) Electrochemical Synthesis of Chelation-Stabilized Organo-Λ ³-Bromanes". ECS Meeting Abstracts MA2023-02, № 52 (2023): 2503. http://dx.doi.org/10.1149/ma2023-02522503mtgabs.

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The chemistry of hypervalent halogen species has made enormous progress over the last few decades, and hypervalent iodine(III) compounds have become common reagents in nowadays organic synthesis. The related isoelectronic hypervalent bromine(III) species feature superior reactivity to the I(III) counterparts due to the higher oxidizing ability, stronger electrophilicity and better leaving group ability (nucleofugality) of the bromanyl moiety. However, the hypervalent bromine chemistry appears to be significantly less developed than that of the iodine(III) compounds. This notable imbalance appe

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29

Eljo, Jasmin, Myriam Carle, and Graham Murphy. "Hypervalent Iodine-Based Activation of Triphenylphosphine for the Functionalization of Alcohols." Synlett 28, no. 20 (2017): 2871–75. http://dx.doi.org/10.1055/s-0036-1589069.

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The use of hypervalent iodine reagents as a general tool for the activation of PPh3 and its application to the functionalization of alcohols is reported. Combination of PPh3 with PhICl2 or TolIF2 gives dihalophosphoranes that are characterized by 31P NMR, however, with PhIOAc2, PhI(OTFA)2, or the cyclic chloro(benzoyloxy)iodane, no phosphoranes were observed. Reaction of these iodanes with PPh3 in the presence of primary, secondary, or tertiary alcohols results in either halogenation or acyl-transfer products in moderate to high yield.

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30

Yannacone, Seth, Vytor Oliveira, Niraj Verma та Elfi Kraka. "A Continuum from Halogen Bonds to Covalent Bonds: Where Do λ3 Iodanes Fit?" Inorganics 7, № 4 (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

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31

Lee, Choi, and Hong. "Alkene Difunctionalization Using Hypervalent Iodine Reagents: Progress and Developments in the Past Ten Years." Molecules 24, no. 14 (2019): 2634. http://dx.doi.org/10.3390/molecules24142634.

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Hypervalent iodine reagents are of considerable relevance in organic chemistry as they can provide a complementary reaction strategy to the use of traditional transition metal chemistry. Over the past two decades, there have been an increasing number of applications including stoichiometric oxidation and catalytic asymmetric variations. This review outlines the main advances in the past 10 years in regard to alkene heterofunctionalization chemistry using achiral and chiral hypervalent iodine reagents and catalysts.

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Ghosh, Soumen, Suman Pradhan, and Indranil Chatterjee. "A survey of chiral hypervalent iodine reagents in asymmetric synthesis." Beilstein Journal of Organic Chemistry 14 (May 30, 2018): 1244–62. http://dx.doi.org/10.3762/bjoc.14.107.

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The recent years have witnessed a remarkable growth in the area of chiral hypervalent iodine chemistry. These environmentally friendly, mild and economic reagents have been used in catalytic or stoichiometric amounts as an alternative to transition metals for delivering enantioenriched molecules. Varieties of different chiral reagents and their use for demanding asymmetric transformations have been documented over the last 25 years. This review highlights the contribution of different chiral hypervalent iodine reagents in diverse asymmetric conversions.

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China, Hideyasu, Nami Kageyama, Hotaka Yatabe, Naoko Takenaga, and Toshifumi Dohi. "Practical Synthesis of 2-Iodosobenzoic Acid (IBA) without Contamination by Hazardous 2-Iodoxybenzoic Acid (IBX) under Mild Conditions." Molecules 26, no. 7 (2021): 1897. http://dx.doi.org/10.3390/molecules26071897.

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We report a convenient and practical method for the preparation of nonexplosive cyclic hypervalent iodine(III) oxidants as efficient organocatalysts and reagents for various reactions using Oxone® in aqueous solution under mild conditions at room temperature. The thus obtained 2-iodosobenzoic acids (IBAs) could be used as precursors of other cyclic organoiodine(III) derivatives by the solvolytic derivatization of the hydroxy group under mild conditions of 80 °C or lower temperature. These sequential procedures are highly reliable to selectively afford cyclic hypervalent iodine compounds in exc

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34

Cavallo, Gabriella, Jane S. Murray, Peter Politzer, Tullio Pilati, Maurizio Ursini, and Giuseppe Resnati. "Halogen bonding in hypervalent iodine and bromine derivatives: halonium salts." IUCrJ 4, no. 4 (2017): 411–19. http://dx.doi.org/10.1107/s2052252517004262.

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Halogen bonds have been identified in a series of ionic compounds involving bromonium and iodonium cations and several different anions, some also containing hypervalent atoms. The hypervalent bromine and iodine atoms in the examined compounds are found to have positive σ-holes on the extensions of their covalent bonds, while the hypervalent atoms in the anions have negative σ-holes. The positive σ-holes on the halogens of the studied halonium salts determine the linearity of the short contacts between the halogen and neutral or anionic electron donors, as usual in halogen bonds.

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35

Hirashima, Mayu, Syotaro Hamatani, Hirotaka Sasa, Naoko Takenaga, Tomonori Hanasaki, and Toshifumi Dohi. "Metal-Free Synthesis of Benzimidazolinones via Oxidative Cyclization Under Hypervalent Iodine Catalysis." Chemistry 7, no. 2 (2025): 50. https://doi.org/10.3390/chemistry7020050.

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Benzimidazolinones exhibit unique biological activities and serve as building blocks in synthesizing pharmaceutical compounds. Although multiple synthetic approaches involving intermolecular cyclization reactions have been reported, intramolecular cyclization reactions are scarce, and more rational synthetic methods are required. Hypervalent iodine-catalyzed oxidative C–N coupling is a potentially effective approach for synthesizing benzimidazolinones under metal-free conditions. In this study, we present a method utilizing hypervalent iodine catalysis for the oxidative cyclization of N’-aryl

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36

Shea, Michael T., Gregory T. Rohde, Yulia A. Vlasenko, et al. "Convenient Synthesis of Benziodazolone: New Reagents for Direct Esterification of Alcohols and Amidation of Amines." Molecules 26, no. 23 (2021): 7355. http://dx.doi.org/10.3390/molecules26237355.

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Hypervalent iodine heterocycles represent one of the important classes of hypervalent iodine reagents with many applications in organic synthesis. This paper reports a simple and convenient synthesis of benziodazolones by the reaction of readily available iodobenzamides with m-chloroperoxybenzoic acid in acetonitrile at room temperature. The structure of one of these new iodine heterocycles was confirmed by X-ray analysis. In combination with PPh3 and pyridine, these benziodazolones can smoothly react with alcohols or amines to produce the corresponding esters or amides of 3-chlorobenzoic acid

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37

Chen, Ling-Ching, and Huey-Min Wang. "DE(MONOTHIO)ACETALIZATION INDUCED BY HYPERVALENT IODINE AND SODIUM IODIDE." Organic Preparations and Procedures International 31, no. 5 (1999): 562–64. http://dx.doi.org/10.1080/00304949909355341.

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38

Dahiya, Anjali, Ashish Kumar Sahoo, Nikita Chakraborty, Bubul Das, and Bhisma K. Patel. "Updates on hypervalent-iodine reagents: metal-free functionalisation of alkenes, alkynes and heterocycles." Organic & Biomolecular Chemistry 20, no. 10 (2022): 2005–27. http://dx.doi.org/10.1039/d1ob02233d.

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Yoshimura, Akira, Khiem C. Nguyen, Scott C. Klasen, Akio Saito, Victor N. Nemykin, and Viktor V. Zhdankin. "Preparation, structure, and versatile reactivity of pseudocyclic benziodoxole triflate, new hypervalent iodine reagent." Chemical Communications 51, no. 37 (2015): 7835–38. http://dx.doi.org/10.1039/c5cc02009c.

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40

Shao, Yingbo, Zhiyuan Ren, Zhihui Han, Li Chen, Yao Li, and Xiao-Song Xue. "Predicting bond dissociation energies of cyclic hypervalent halogen reagents using DFT calculations and graph attention network model." Beilstein Journal of Organic Chemistry 20 (June 28, 2024): 1444–52. http://dx.doi.org/10.3762/bjoc.20.127.

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Although hypervalent iodine(III) reagents have become staples in organic chemistry, the exploration of their isoelectronic counterparts, namely hypervalent bromine(III) and chlorine(III) reagents, has been relatively limited, partly due to challenges in synthesizing and stabilizing these compounds. In this study, we conduct a thorough examination of both homolytic and heterolytic bond dissociation energies (BDEs) critical for assessing the chemical stability and functional group transfer capability of cyclic hypervalent halogen compounds using density functional theory (DFT) analysis. A modera

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41

Katayev, D., J. Václavík, F. Brüning, B. Commare та A. Togni. "Synthesis of quaternary α-perfluoroalkyl lactams via electrophilic perfluoroalkylation". Chemical Communications 52, № 21 (2016): 4049–52. http://dx.doi.org/10.1039/c6cc00700g.

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42

Ma, Xueji, Aili Sun, and Kai-Kai Wang. "Unexpected ester and phosphonate radical generation by hypervalent iodine compounds for synthesizing 6-phenanthridine derivatives." New Journal of Chemistry 46, no. 15 (2022): 6856–59. http://dx.doi.org/10.1039/d2nj01186g.

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Nakamura, Akira, Hodaka Kanou, Junki Tanaka, Akira Imamiya, Tomohiro Maegawa, and Yasuyoshi Miki. "A mild method for synthesizing carboxylic acids by oxidation of aldoximes using hypervalent iodine reagents." Organic & Biomolecular Chemistry 16, no. 4 (2018): 541–44. http://dx.doi.org/10.1039/c7ob02858j.

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Morelli, Paola, Xavier Martin-Benlloch, Romain Tessier, Jerome Waser, Naomi Sakai, and Stefan Matile. "Ethynyl benziodoxolones: functional terminators for cell-penetrating poly(disulfide)s." Polymer Chemistry 7, no. 20 (2016): 3465–70. http://dx.doi.org/10.1039/c6py00562d.

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Zhang, Guangtao, Yuanxun Wang, Jun Xu, et al. "A new hypervalent iodine(iii/v) oxidant and its application to the synthesis of 2H-azirines." Chemical Science 11, no. 4 (2020): 947–53. http://dx.doi.org/10.1039/c9sc05536c.

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The reaction of o-nitroiodobenzene and mCPBA in AcOH was found to afford a novel hypervalent iodine compound which both iodine(iii) and iodine(v) moieties coexist. This new reagent is proved to be effective in realizing the synthesis of 2H-azirines.

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Wegeberg, Christina, Christian Grundahl Frankær, and Christine J. McKenzie. "Reduction of hypervalent iodine by coordination to iron(iii) and the crystal structures of PhIO and PhIO2." Dalton Transactions 45, no. 44 (2016): 17714–22. http://dx.doi.org/10.1039/c6dt02937j.

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Iodine L<sub>3</sub>-edge XANES spectra using reference compounds with formal iodine oxidation states spanning −1 to +7 show that iodine in an Fe(iii) coordinated iodosylbenzene (PhIO) is reduced compared to parent hypervalent PhIO which has been structurally characterized.

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Boelke, Andreas, Peter Finkbeiner, and Boris J. Nachtsheim. "Atom-economical group-transfer reactions with hypervalent iodine compounds." Beilstein Journal of Organic Chemistry 14 (May 30, 2018): 1263–80. http://dx.doi.org/10.3762/bjoc.14.108.

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Hypervalent iodine compounds, in particular aryl-λ3-iodanes, have been used extensively as electrophilic group-transfer reagents. Even though these compounds are superior substrates in terms of reactivity and stability, their utilization is accompanied by stoichiometric amounts of an aryl iodide as waste. This highly nonpolar side product can be tedious to separate from the desired target molecules and significantly reduces the overall atom efficiency of these transformations. In this short review, we want to give a brief summary of recently developed methods, in which this arising former wast

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Singh, Fateh V., and Thomas Wirth. "Hypervalent iodine chemistry and light: photochemical reactions involving hypervalent iodine chemistry." Arkivoc 2021, no. 7 (2021): 12–47. http://dx.doi.org/10.24820/ark.5550190.p011.483.

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Zhang, Yang, Hua Tan та Weibing Liu. "Synthesis of α-sulfonyloxyketones via iodobenzene diacetate (PIDA)-mediated oxysulfonyloxylation of alkynes with sulfonic acids". RSC Advances 7, № 85 (2017): 54017–20. http://dx.doi.org/10.1039/c7ra11875a.

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Sakamoto, Ryu, Hirotaka Kashiwagi, Sermadurai Selvakumar, Shin A. Moteki, and Keiji Maruoka. "Efficient generation of perfluoroalkyl radicals from sodium perfluoroalkanesulfinates and a hypervalent iodine(iii) reagent: mild, metal-free synthesis of perfluoroalkylated organic molecules." Organic & Biomolecular Chemistry 14, no. 27 (2016): 6417–21. http://dx.doi.org/10.1039/c6ob01245k.

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