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Special Issue "Hypervalent Iodine Chemistry"

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (10 February 2017)

Special Issue Editors

Guest Editor
Dr. Wesley Moran

Department of Chemistry, University of Huddersfield, Queensgate, Huddersfield HD1 3DH, UK
Website | E-Mail
Interests: : hypervalent iodine chemistry; C-H functionalization; organocatalysis; metal catalysis; organic synthesis
Guest Editor
Dr. Arantxa Rodríguez

Department of Chemistry, University of Huddersfield, Queensgate, Huddersfield HD1 3DH, UK
E-Mail
Interests: hypervalent iodine chemistry; transition metal-catalysed reactions; synthetic methodology; drug development; computational chemistry

Special Issue Information

Dear Colleagues,

Hypervalent iodine chemistry has matured over several decades, with many transformations mediated by hypervalent iodine compounds now being commonplace in synthesis. In particular, the ability to use these species in place of expensive or toxic metal salts is appealing. They have been used as stoichiometric oxidants, as functional group transfer agents, and as sources of radicals and carbenes. Recent advances include the development of enantioselective processes with chiral hypervalent iodine compounds and the realisation of catalytic reactions with in situ generated hypervalent iodine species.

This Special Issue will focus on the latest developments in hypervalent iodine chemistry in all areas of synthesis.

Dr. Wesley Moran
Dr. Arantxa Rodríguez
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 papers will be 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 1800 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

  • reactivity
  • enantioselectivity
  • preparation
  • radical reactions
  • transition metal-catalyzed reactions
  • computational studies
  • organocatalysts
  • halogenation
  • homocoupling
  • C-C bond formation

Published Papers (4 papers)

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Research

Open AccessArticle
Hypervalent Iodine(III)-Induced Domino Oxidative Cyclization for the Synthesis of Cyclopenta[b]furans
Molecules 2016, 21(12), 1713; https://doi.org/10.3390/molecules21121713
Received: 17 November 2016 / Revised: 12 December 2016 / Accepted: 14 December 2016 / Published: 21 December 2016
Cited by 1 | PDF Full-text (2661 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
A new strategy for cyclopenta[b]furan synthesis mediated by hypervalent iodine(III) has been described. The approach employs diacetoxyiodobenzene-induced initial dehydrogenation to a putative trienone intermediate and triggered sequential cycloisomerization to form the cyclo-penta[b]furan targets. Full article
(This article belongs to the Special Issue Hypervalent Iodine Chemistry)
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Open AccessArticle
Aqueous DMSO Mediated Conversion of (2-(Arylsulfonyl)vinyl)iodonium Salts to Aldehydes and Vinyl Chlorides
Molecules 2016, 21(8), 1073; https://doi.org/10.3390/molecules21081073
Received: 20 July 2016 / Revised: 4 August 2016 / Accepted: 6 August 2016 / Published: 16 August 2016
Cited by 4 | PDF Full-text (1144 KB) | HTML Full-text | XML Full-text
Abstract
Vinyl(aryl)iodonium salts are useful compounds in organic synthesis but they are under-utilized and their chemistry is under-developed. Herein is described the solvolysis of some vinyl(phenyl)iodonium salts, bearing an arylsulfonyl group, in aqueous DMSO leading to aldehyde formation. This unusual process is selective and [...] Read more.
Vinyl(aryl)iodonium salts are useful compounds in organic synthesis but they are under-utilized and their chemistry is under-developed. Herein is described the solvolysis of some vinyl(phenyl)iodonium salts, bearing an arylsulfonyl group, in aqueous DMSO leading to aldehyde formation. This unusual process is selective and operates under ambient conditions. Furthermore, the addition of aqueous HCl and DMSO to these vinyl(aryl)iodonium salts allows their facile conversion to vinyl chlorides. Full article
(This article belongs to the Special Issue Hypervalent Iodine Chemistry)
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Open AccessArticle
Metathetical Redox Reaction of (Diacetoxyiodo)arenes and Iodoarenes
Molecules 2015, 20(12), 22635-22644; https://doi.org/10.3390/molecules201219874
Received: 25 November 2015 / Revised: 10 December 2015 / Accepted: 15 December 2015 / Published: 17 December 2015
Cited by 9 | PDF Full-text (2718 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
The oxidation of iodoarenes is central to the field of hypervalent iodine chemistry. It was found that the metathetical redox reaction between (diacetoxyiodo)arenes and iodoarenes is possible in the presence of a catalytic amount of Lewis acid. This discovery opens a new strategy [...] Read more.
The oxidation of iodoarenes is central to the field of hypervalent iodine chemistry. It was found that the metathetical redox reaction between (diacetoxyiodo)arenes and iodoarenes is possible in the presence of a catalytic amount of Lewis acid. This discovery opens a new strategy to access (diacetoxyiodo)arenes. A computational study is provided to rationalize the results observed. Full article
(This article belongs to the Special Issue Hypervalent Iodine Chemistry)
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Open AccessArticle
Stereoselective Formation of Substituted 1,3-Dioxolanes through a Three-Component Assembly during the Oxidation of Alkenes with Hypervalent Iodine(III)
Molecules 2015, 20(9), 17041-17057; https://doi.org/10.3390/molecules200917041
Received: 14 August 2015 / Revised: 9 September 2015 / Accepted: 11 September 2015 / Published: 17 September 2015
Cited by 5 | PDF Full-text (790 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Stereoselective formation of substituted 1,3-dioxolanes was achieved through an assembly of three components: alkene, carboxylic acid and silyl enol ether. The reaction proceeded via stereospecific generation of a 1,3-dioxolan-2-yl cation intermediate during oxidation of alkene substrates with hypervalent iodine. The stereoselective trapping of [...] Read more.
Stereoselective formation of substituted 1,3-dioxolanes was achieved through an assembly of three components: alkene, carboxylic acid and silyl enol ether. The reaction proceeded via stereospecific generation of a 1,3-dioxolan-2-yl cation intermediate during oxidation of alkene substrates with hypervalent iodine. The stereoselective trapping of the cation intermediate with silyl enol ether completed the formation of the dioxolane product. Full article
(This article belongs to the Special Issue Hypervalent Iodine Chemistry)
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Graphical abstract

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