Chemistry of Polyvalent Iodine
TLDR
The present review summarizes the data that appeared in the literature following publication of previous reviews in 1996 and 2002 and is organized according to the classes of organic polyvalent iodine compounds with emphasis on their synthetic application.Abstract:
Starting from the early 1990’s, the chemistry of polyvalent iodine organic compounds has experienced an explosive development. This surging interest in iodine compounds is mainly due to the very useful oxidizing properties of polyvalent organic iodine reagents, combined with their benign environmental character and commercial availability. Iodine(III) and iodine(V) derivatives are now routinely used in organic synthesis as reagents for various selective oxidative transformations of complex organic molecules. Several areas of hypervalent organoiodine chemistry have recently attracted especially active interest and research activity. These areas, in particular, include the synthetic applications of 2-iodoxybenzoic acid (IBX) and similar oxidizing reagents based on the iodine(V) derivatives, the development and synthetic use of polymer-supported and recyclable polyvalent iodine reagents, the catalytic applications of organoiodine compounds, and structural studies of complexes and supramolecular assemblies of polyvalent iodine compounds.
The chemistry of polyvalent iodine has previously been covered in four books1–4 and several comprehensive review papers.5–17 Numerous reviews on specific classes of polyvalent iodine compounds and their synthetic applications have recently been published.18–61 Most notable are the specialized reviews on [hydroxy(tosyloxy)iodo]benzene,41 the chemistry and synthetic applications of iodonium salts,29,36,38,42,43,46,47,54,55 the chemistry of iodonium ylides,56–58 the chemistry of iminoiodanes,28 hypervalent iodine fluorides,27 electrophilic perfluoroalkylations,44 perfluoroorgano hypervalent iodine compounds,61 the chemistry of benziodoxoles,24,45 polymer-supported hypervalent iodine reagents,30 hypervalent iodine-mediated ring contraction reactions,21 application of hypervalent iodine in the synthesis of heterocycles,25,40 application of hypervalent iodine in the oxidation of phenolic compounds,32,34,50–53,60 oxidation of carbonyl compounds with organohypervalent iodine reagents,37 application of hypervalent iodine in (hetero)biaryl coupling reactions,31 phosphorolytic reactivity of o-iodosylcarboxylates,33 coordination of hypervalent iodine,19 transition metal catalyzed reactions of hypervalent iodine compounds,18 radical reactions of hypervalent iodine,35,39 stereoselective reactions of hypervalent iodine electrophiles,48 catalytic applications of organoiodine compounds,20,49 and synthetic applications of pentavalent iodine reagents.22,23,26,59
The main purpose of the present review is to summarize the data that appeared in the literature following publication of our previous reviews in 1996 and 2002. In addition, a brief introductory discussion of the most important earlier works is provided in each section. The review is organized according to the classes of organic polyvalent iodine compounds with emphasis on their synthetic application. Literature coverage is through July 2008.read more
Citations
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Journal ArticleDOI
Advances in Synthetic Applications of Hypervalent Iodine Compounds
TL;DR: One of the goals of this Review is to attract the attention of the scientific community as to the benefits of using hypervalent iodine compounds as an environmentally sustainable alternative to heavy metals.
Journal ArticleDOI
Diaryliodonium Salts: A Journey from Obscurity to Fame
TL;DR: An overview of the historical and recent advances in the synthesis and applications of diaryliodonium salts is provided.
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Transition-Metal-Free Coupling Reactions
TL;DR: This research presents a new generation of state-of-the-art materials for bioorganic and non-volatile organometallic research that combines high-performance liquid chromatography and high-tech materials for organic synthesis.
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Light-Controlled Radical Polymerization: Mechanisms, Methods, and Applications
TL;DR: A comprehensive survey of photo-CRP reactions can be found in this article, where a large number of methods are summarized and further classified into subcategories based on the specific reagents, catalysts, etc., involved.
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Light-Controlled Radical Polymerization: Mechanisms, Methods, and Applications
TL;DR: This review provides a comprehensive survey of photocontrolled, living radical polymerizations (photo-CRPs), and a large number of methods are summarized and further classified into subcategories based on the specific reagents, catalysts, etc., involved.
References
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Readily accessible 12-I-5 oxidant for the conversion of primary and secondary alcohols to aldehydes and ketones
D. B. Dess,J. C. Martin +1 more
TL;DR: Conversion de cyclohexanol, octanol, alcool benzylique and des alcools dimethoxy-and trimethoxy benzyliques par oxydation avec le triacetoxy-1, 1, 1 benzoiodoxole-1 2 one-3
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A useful 12-I-5 triacetoxyperiodinane (the Dess-Martin periodinane) for the selective oxidation of primary or secondary alcohols and a variety of related 12-I-5 species
Daniel B. Dess,J. C. Martin +1 more
Journal ArticleDOI
Recent Developments in the Chemistry of Polyvalent Iodine Compounds
Journal ArticleDOI
A Highly Selective Catalytic Method for the Oxidative Functionalization of C−H Bonds
TL;DR: A new and highly practical Pd(II)-catalyzed method for the regio- and chemoselective oxidative functionalization of arenes and alkanes and a preliminary catalytic cycle is proposed.
Related Papers (5)
Recent Developments in the Chemistry of Polyvalent Iodine Compounds
Hypervalent iodine reagents as a new entrance to organocatalysts
Toshifumi Dohi,Yasuyuki Kita +1 more