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Author: Grafiati

Published: 19 October 2024

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1

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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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 bonding.

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3

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 (January 17, 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 combination of strain and hypervalent bonding, and the way they work in concert to yield this unusual case of multiple hypervalence, has potential for extension to a broader range of solid-state compounds.

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4

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 (June 1, 2007): 871–72. http://dx.doi.org/10.1515/znb-2007-0619.

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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 to be unreactive under similar conditions, despite the weaker C–H bond. A preliminary mechanistic analysis suggests that this NHPI-iodate system is functioning by a radical-based mechanism where iodine generated in situ captures formed benzylic radicals. The benzylic iodide intermediate then solvolyzes to yield the product ester.

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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 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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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 (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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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 (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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9

Xing, Linlin, Yong Zhang, and Yunfei Du. "Hypervalent Iodine-Mediated Synthesis of Spiroheterocycles via Oxidative Cyclization." Current Organic Chemistry 23, no. 1 (March 13, 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, 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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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 spirocyclic scaffolds using hypervalent iodine reagents are covered including their stereoselective synthesis. Additionally, the applications of these reagents in natural product synthesis are also covered.

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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, Dongke Zhang, Haofeng Shi, Zhenyang Yu, Shanqing Tao, and Yunfei Du. "Formation of Carbon-Carbon Bonds Mediated by Hypervalent Iodine Reagents Under Metal-free Conditions." Current Organic Chemistry 24, no. 1 (April 15, 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 (November 8, 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 exploit the organocatalytic activation of the hypervalent iodine reagent itself.1 Introduction2 Organocatalytic Activation of Acceptor2.1 Amine Catalysis via Enamine and Unsaturated Iminium Formation2.2 NHC Catalysis via Acyl Anion Equivalent and Enolate Formation2.3 Chiral Cation Directed Catalysis and Brønsted Base Catalysis via Pairing with Stabilized Enolates3 Organocatalytic Activation of Hypervalent Iodine Reagent3.1 Brønsted and Lewis Acid Catalysis3.2 Lewis Base Catalysis3.3 Radical Reactions with Organic Promoters and Catalysts4 Summary and Outlook

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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 (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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17

Maegawa, Tomohiro, Ayako Shibata, Sara Kitamoto, Kazuma Fujimura, Yuuka Hirose, Hiromi Hamamoto, Akira Nakamura, and Yasuyoshi Miki. "Dehydroxymethyl Bromination of Alkoxybenzyl Alcohols by Using a Hypervalent Iodine Reagent and Lithium Bromide." Synlett 29, no. 17 (September 26, 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-mediated glycosylation allowed us to couple a nucleobase with cyclic allylsilanes and glycal derivatives to yield carbocyclic nucleosides and 2’,3’-unsaturated nucleosides, respectively. In addition, the combination of hypervalent iodine and Lewis acid could be used for the glycosylation of glycals and thioglycosides to produce disaccharides. In this paper, we review the use of hypervalent iodine-mediated glycosylation reactions for the synthesis of nucleosides and oligosaccharide derivatives.

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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 (October 16, 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 most popular metal and non-metal involved transformations. However, the comprehensive summary of the comparison of metal and non-metal mediated transformations is still not available. Objective: The review focuses on comparing these two types of reactions (Pd-catalyzed reactions and hypervalent iodine reagent mediated reactions) based on the ways of forming new C–C bonds, as well as the scope and limitations on the demonstration of their synthetic applications. Conclusion: Comparing the Pd-catalyzed strategies and hypervalent iodine reagent mediated methodologies for the direct C–C bond formation from activation of C-H bonds, we clearly noticed that both strategies are powerful tools for directly obtaining the corresponding pruducts. On one hand, the hypervalent iodine reagents mediated reactions are normally under mild conditions and give the molecular diversity without the presence of transition-metal, while the Pd-catalyzed approaches have a broader scope for the wide synthetic applications. On the other hand, unlike Pd-catalyzed C-C bond formation reactions, the study towards hypervalent iodine reagent mediated methodology mainly focused on the stoichiometric amount of hypervalent iodine reagent, while few catalytic reactions have been reported. Meanwhile, hypervalent iodine strategy has been proved to be more efficient in intramolecular medium-ring construction, while there are less successful examples on C(sp3)–C(sp3) bond formation. In summary, we have demonstrated a number of selected approaches for the formation of a new C–C bond under the utilization of Pd-catalyzed reaction conditions or hyperiodine reagents. The direct activations of sp2 or sp3 hybridized C–H bonds are believed to be important strategies for the future molecular design as well as useful chemical entity synthesis.

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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 (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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22

Kotali, Antigoni. "Hypervalent Iodine." Molecules 10, no. 1 (January 31, 2005): 181–82. http://dx.doi.org/10.3390/10010181.

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23

Krylov, Igor B., Stanislav A. Paveliev, Mikhail A. Syroeshkin, Alexander A. Korlyukov, Pavel V. Dorovatovskii, Yan V. Zubavichus, Gennady I. Nikishin, and Alexander O. Terent’ev. "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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24

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 (November 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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25

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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26

Eljo, Jasmin, Myriam Carle, and Graham Murphy. "Hypervalent Iodine-Based Activation of Triphenylphosphine for the Functionalization of Alcohols." Synlett 28, no. 20 (July 12, 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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27

Sokolovs, Igors, Edgars Suna, and Robert Francke. "(Invited) Electrochemical Synthesis of Chelation-Stabilized Organo-Λ ³-Bromanes." ECS Meeting Abstracts MA2023-02, no. 52 (December 22, 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 appears to be due to the relatively low stability and high oxidizing power of bromine(III) reagents, resulting in reactivity that is difficult to control. Furthermore, there is a clear shortage of simple method for the synthesis of bromine (III) species, but known methods often require handling of the highly toxic and corrosive BrF3 precursor. In this context, we have proposed the electrochemical generation of chelation-stabilized hypervalent bromine(III) compounds as a possible solution to the above problems. This presentation will give an overview of our current progress in this field.

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28

Dohi, Toshifumi. "Recent Topics in Iodine Reagents and Compounds in Organic Chemistry." Current Organic Chemistry 26, no. 21 (November 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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29

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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30

Lee, Choi, and Hong. "Alkene Difunctionalization Using Hypervalent Iodine Reagents: Progress and Developments in the Past Ten Years." Molecules 24, no. 14 (July 19, 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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31

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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32

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 (March 27, 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 excellent yields without contamination by hazardous pentavalent iodine(III) compound.

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33

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 (May 10, 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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34

Shea, Michael T., Gregory T. Rohde, Yulia A. Vlasenko, Pavel S. Postnikov, Mekhman S. Yusubov, Viktor V. Zhdankin, Akio Saito, and Akira Yoshimura. "Convenient Synthesis of Benziodazolone: New Reagents for Direct Esterification of Alcohols and Amidation of Amines." Molecules 26, no. 23 (December 3, 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, respectively. It was found that the novel benziodazolone reagent reacts more efficiently than the analogous benziodoxolone reagent in this esterification.

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35

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 (October 1999): 562–64. http://dx.doi.org/10.1080/00304949909355341.

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36

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 moderate linear correlation was observed between the homolytic BDEs across different halogen centers, while a strong linear correlation was noted among the heterolytic BDEs across these centers. Furthermore, we developed a predictive model for both homolytic and heterolytic BDEs of cyclic hypervalent halogen compounds using machine learning algorithms. The results of this study could aid in estimating the chemical stability and functional group transfer capabilities of hypervalent bromine(III) and chlorine(III) reagents, thereby facilitating their development.

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37

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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38

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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39

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 waste is used as an additional reagent in cascade transformations to generate multiple substituted products in one step and with high atom efficiency.

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40

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

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41

Zhang, Guangtao, Yuanxun Wang, Jun Xu, Jiyun Sun, Fengxia Sun, Yilin Zhang, Chenglin Zhang, and Yunfei Du. "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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42

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 L₃-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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43

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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44

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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45

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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46

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

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47

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

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48

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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49

Radzhabov, Maxim R., Aleksei B. Sheremetev, and Tatyana S. Pivina. "Oxidative ability of organic iodine(iii) reagents: a theoretical assessment." New Journal of Chemistry 44, no. 17 (2020): 7051–57. http://dx.doi.org/10.1039/d0nj00837k.

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Computational prediction of the oxidative ability of hypervalent iodine reagents was performed based on redox potentials, calculated at the B3LYP/6-311+G(d,p) level of theory with the SDD ECP46MDF pseudopotential for the iodine atom.

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50

Cortés González, Miguel A., Xingguo Jiang, Patrik Nordeman, Gunnar Antoni, and Kálmán J. Szabó. "Rhodium-mediated 18F-oxyfluorination of diazoketones using a fluorine-18-containing hypervalent iodine reagent." Chemical Communications 55, no. 89 (2019): 13358–61. http://dx.doi.org/10.1039/c9cc06905d.

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