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Hypervalent Iodine Chemistry
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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) | Viewed by 23757

Special Issue Editors

Dr. Wesley Moran

E-Mail Website
Guest Editor
School of Pharmacy & Bioengineering, Keele University, Keele, Staffordshire ST5 5BG, UK
Interests: organic chemistry; catalysis; iodine; electrochemical synthesis; heterocycles; reaction mechanisms
Dr. Arantxa Rodríguez

E-Mail
Guest Editor
Department of Chemistry, University of Huddersfield, Queensgate, Huddersfield HD1 3DH, UK
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 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

  • 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

2661 KiB  
Article
Hypervalent Iodine(III)-Induced Domino Oxidative Cyclization for the Synthesis of Cyclopenta[b]furans
by Mei-Huey Lin, Yu-Chun Chen, Shih-Hao Chiu, Yun-Fan Chen and Tsung-Hsun Chuang
Molecules 2016, 21(12), 1713; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules21121713 - 21 Dec 2016
Cited by 2 | Viewed by 4723
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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1144 KiB  
Article
Aqueous DMSO Mediated Conversion of (2-(Arylsulfonyl)vinyl)iodonium Salts to Aldehydes and Vinyl Chlorides
by Eman Zawia and Wesley J. Moran
Molecules 2016, 21(8), 1073; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules21081073 - 16 Aug 2016
Cited by 9 | Viewed by 4951
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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2718 KiB  
Article
Metathetical Redox Reaction of (Diacetoxyiodo)arenes and Iodoarenes
by Antoine Jobin-Des Lauriers and Claude Y. Legault
Molecules 2015, 20(12), 22635-22644; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules201219874 - 17 Dec 2015
Cited by 18 | Viewed by 7384
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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790 KiB  
Article
Stereoselective Formation of Substituted 1,3-Dioxolanes through a Three-Component Assembly during the Oxidation of Alkenes with Hypervalent Iodine(III)
by Mio Shimogaki, Morifumi Fujita and Takashi Sugimura
Molecules 2015, 20(9), 17041-17057; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules200917041 - 17 Sep 2015
Cited by 13 | Viewed by 6126
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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