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Advances in the Chemistry of Hypervalent Iodine Compounds
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Advances in the Chemistry of Hypervalent Iodine Compounds

A special issue of Molecules (ISSN 1420-3049).

Deadline for manuscript submissions: closed (30 June 2019) | Viewed by 26031

Special Issue Editor

Dr. Kazunori Miyamoto

E-Mail Website1 Website2
Guest Editor
Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, Japan
Interests: hypervalent iodine chemistry; hypervalent bromine and chlorine chemistry; chemistry of reactive intermediate; kinetic studies; theoretical chemistry; photochemistry; supramolecular chemistry

Special Issue Information

Dear Colleagues,

Hypervalent compounds have attracted great attention from organic and inorganic/physical/theoretical chemists, owing to their unique structural characteristics and reactivity. In particular, Group 17 elements, hypervalent compounds have enjoyed widespread application over recent decades. Especially, 5th period hypervalent iodine compounds have become increasingly important in modern organic synthesis, mainly because of their: (1) excellent reactivity arising from vastly enhanced nucleofugality; (2) high chemoselectivity; (3) environmentally friendly nature; and (4) distinctive safety record (low-toxicity, non-explosiveness). In this Special Issue, we invite articles and communications from colleagues who have investigated the chemistry of hypervalent iodine compounds (and related hypervalent bromine/chlorine compounds), including their synthesis, characterization, reaction and their application in materials synthesis. Specifically, spectroscopic, crystallographic, and theoretical analyses as well as photochemical, electrochemical, and mechanochemical reactions would be suitable for this Special Issue. The editors hope very much to receive many interesting and challenging research manuscripts on these topics.

Dr. Kazunori Miyamoto
Guest Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • Hypervalent iodine
  • Photochemistry
  • Electorochemistry
  • Theoretical studies
  • Mechanochemistry
  • Analytical chemistry
  • Materials science

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Published Papers (5 papers)

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Research

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7 pages, 1051 KiB  
Article
One-Step Synthesis of N-Succinimidyl-4-[18F]Fluorobenzoate ([18F]SFB)
by Ida Nymann Petersen, Jacob Madsen, Christian Bernard Matthijs Poulie, Andreas Kjær and Matthias Manfred Herth
Molecules 2019, 24(19), 3436; https://doi.org/10.3390/molecules24193436 - 22 Sep 2019
Cited by 11 | Viewed by 3196
Abstract
Herein, we present a one-step labeling procedure of N-succinimidyl-4-[18F]-fluorobenzoate ([18F]SFB) starting from spirocyclic iodonium ylide precursors. Precursor syntheses succeeded via a simple one-pot, two-step synthesis sequence, in yields of approximately 25%. Subsequent 18F-nucleophilic aromatic labeling was performed, [...] Read more.
Herein, we present a one-step labeling procedure of N-succinimidyl-4-[18F]-fluorobenzoate ([18F]SFB) starting from spirocyclic iodonium ylide precursors. Precursor syntheses succeeded via a simple one-pot, two-step synthesis sequence, in yields of approximately 25%. Subsequent 18F-nucleophilic aromatic labeling was performed, and radiochemical incorporations (RCCs) from 5–35% were observed. Purification could be carried out using HPLC and subsequent solid phase extraction. Radiochemical purity (RCP) of >95% was determined. The total synthesis time, including purification and formulation, was no longer than 60 min. In comparison to the established 3-step synthesis route of [18F]SFB, this one-step approach avoids formation of volatile radioactive side-products and simplifies automatization. Full article
(This article belongs to the Special Issue Advances in the Chemistry of Hypervalent Iodine Compounds)
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13 pages, 6507 KiB  
Article
Synthesis of Uracil-Iodonium(III) Salts for Practical Utilization as Nucleobase Synthetic Modules
by Naoko Takenaga, Takumi Hayashi, Shohei Ueda, Hiroyuki Satake, Yoichi Yamada, Tetsuya Kodama and Toshifumi Dohi
Molecules 2019, 24(17), 3034; https://doi.org/10.3390/molecules24173034 - 21 Aug 2019
Cited by 8 | Viewed by 4955
Abstract
Iodonium(III) salts bearing uracil moieties have recently appeared in the literature, but their structural scope and utilization are limited because of their hygroscopic characteristics. In this study, we describe our detailed investigations for synthesizing a series of uracil iodonium(III) salts derived with various [...] Read more.
Iodonium(III) salts bearing uracil moieties have recently appeared in the literature, but their structural scope and utilization are limited because of their hygroscopic characteristics. In this study, we describe our detailed investigations for synthesizing a series of uracil iodonium(III) salts derived with various structural motifs and counterions. These new compounds have been utilized as attractive synthetic modules in constructing functionalized nucleobase and nucleosides. Full article
(This article belongs to the Special Issue Advances in the Chemistry of Hypervalent Iodine Compounds)
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13 pages, 3064 KiB  
Article
Cu-Catalyzed Oxidative 3-Amination of Indoles via Formation of Indolyl(aryl)iodonium Imides Using o-Substituted (Diacetoxyiodo)arene as a High-Performance Hypervalent Iodine Compound
by Kazuhiro Watanabe and Katsuhiko Moriyama
Molecules 2019, 24(6), 1147; https://doi.org/10.3390/molecules24061147 - 22 Mar 2019
Cited by 5 | Viewed by 3742
Abstract
An oxidative 3-amination of indole derivatives using hypervalent iodine(III) and bissulfonimides, which proceeds via the formation of indolyl(aryl)iodonium imides, was developed. This reaction was followed by an indole-selective copper-catalyzed oxidative C–N coupling reaction to obtain 3-amino indole derivatives as single regioisomers. o-Alkoxy(diacetoxyiodo)arenes [...] Read more.
An oxidative 3-amination of indole derivatives using hypervalent iodine(III) and bissulfonimides, which proceeds via the formation of indolyl(aryl)iodonium imides, was developed. This reaction was followed by an indole-selective copper-catalyzed oxidative C–N coupling reaction to obtain 3-amino indole derivatives as single regioisomers. o-Alkoxy(diacetoxyiodo)arenes showed higher reactivity in the reaction than o-alkyl(diacetoxyiodo)arenes, efficiently promoting the formation of indolyl(aryl)iodonium imides in the first step. Full article
(This article belongs to the Special Issue Advances in the Chemistry of Hypervalent Iodine Compounds)
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Graphical abstract

11 pages, 1989 KiB  
Article
Sulfonylimino Group Transfer Reaction Using Imino-λ3-iodanes with I2 as Catalyst Under Metal-free Conditions
by Akira Yoshimura, Cody L. Makitalo, Melissa E. Jarvi, Michael T. Shea, Pavel S. Postnikov, Gregory T. Rohde, Viktor V. Zhdankin, Akio Saito and Mekhman S. Yusubov
Molecules 2019, 24(5), 979; https://doi.org/10.3390/molecules24050979 - 11 Mar 2019
Cited by 12 | Viewed by 4848
Abstract
A new practical procedure of imination for sulfide has been developed. The treatment of (N-tosylimino)-phenyl-λ3-iodane, PhINTs, with various sulfides in the presence of a catalytic amount of I2 under metal-free conditions affords the corresponding N-tosylsulfilimine compounds with [...] Read more.
A new practical procedure of imination for sulfide has been developed. The treatment of (N-tosylimino)-phenyl-λ3-iodane, PhINTs, with various sulfides in the presence of a catalytic amount of I2 under metal-free conditions affords the corresponding N-tosylsulfilimine compounds with moderate to good yields. This facile transfer procedure of the sulfonylimino group can also be applied to triphenylphosphine to produce the respective iminotriphenylphosphoranes in high yields. According to the reaction mechanism studies, the process of imination from (N-tosylimino)-phenyl-λ3-iodane to sulfide under the conditions may involve radical steps within the reaction mechanism. Full article
(This article belongs to the Special Issue Advances in the Chemistry of Hypervalent Iodine Compounds)
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Review

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23 pages, 11957 KiB  
Review
Alkene Difunctionalization Using Hypervalent Iodine Reagents: Progress and Developments in the Past Ten Years
by Ji Hoon Lee, Sungwook Choi and Ki Bum Hong
Molecules 2019, 24(14), 2634; https://doi.org/10.3390/molecules24142634 - 19 Jul 2019
Cited by 72 | Viewed by 8528
Abstract
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 [...] Read more.
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. Full article
(This article belongs to the Special Issue Advances in the Chemistry of Hypervalent Iodine Compounds)
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Scheme 1

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