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      2-Iodoxybenzoic acid ditriflate: the most powerful hypervalent iodine(v) oxidant

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          Abstract

          A new powerful hypervalent iodine( v) oxidant, a ditriflate derivative of 2-iodoxybenzoic acid (IBX), was prepared by the reaction of IBX with trifluoromethanesulfonic acid and characterized by single crystal X-ray crystallography.

          Abstract

          A ditriflate derivative of 2-iodoxybenzoic acid (IBX) was prepared by the reaction of IBX with trifluoromethanesulfonic acid and characterized by single crystal X-ray crystallography. IBX-ditriflate is the most powerful oxidant in a series of structurally similar IBX derivatives which is best illustrated by its ability to readily oxidize hydrocarbons and the oxidation resistant polyfluoroalcohols.

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          Advances in Synthetic Applications of Hypervalent Iodine Compounds.

          Akira Yoshimura, Viktor V Zhdankin (2016)
          The preparation, structure, and chemistry of hypervalent iodine compounds are reviewed with emphasis on their synthetic application. Compounds of iodine possess reactivity similar to that of transition metals, but have the advantage of environmental sustainability and efficient utilization of natural resources. These compounds are widely used in organic synthesis as selective oxidants and environmentally friendly reagents. Synthetic uses of hypervalent iodine reagents in halogenation reactions, various oxidations, rearrangements, aminations, C-C bond-forming reactions, and transition metal-catalyzed reactions are summarized and discussed. Recent discovery of hypervalent catalytic systems and recyclable reagents, and the development of new enantioselective reactions using chiral hypervalent iodine compounds represent a particularly important achievement in the field of hypervalent iodine chemistry. 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.
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            Hypervalent Iodine Chemistry

            Viktor V Zhdankin (2013)
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              Organoiodine(V) reagents in organic synthesis.

              Viktor V Zhdankin (2011)
              Organohypervalent iodine reagents have attracted significant recent interest as versatile and environmentally benign oxidants with numerous applications in organic synthesis. This Perspective summarizes synthetic applications of hypervalent iodine(V) reagents: 2-iodoxybenzoic acid (IBX), Dess-Martin periodinane (DMP), pseudocyclic iodylarenes, and their recyclable polymer-supported analogues. Recent advances in the development of new catalytic systems based on the generation of hypervalent iodine species in situ are also overviewed.
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                Author and article information

                Contributors
                Akira Yoshimura: (View ORCID Profile)
                Thomas Wirth: (View ORCID Profile)
                Journal
                Journal ID (publisher-id): CHCOFS
                Title: Chemical Communications
                Abbreviated Title: Chem. Commun.
                Publisher: Royal Society of Chemistry (RSC)
                ISSN (Print): 1359-7345
                ISSN (Electronic): 1364-548X
                Publication date Created: July 2 2019
                Publication date (Electronic): 2019
                Volume: 55
                Issue: 54
                Pages: 7760-7763
                Affiliations
                [1 ]The Tomsk Polytechnic University
                [2 ]634050 Tomsk
                [3 ]Russia
                [4 ]Tomsk State University
                [5 ]Department of Chemistry and Biochemistry
                [6 ]University of Minnesota
                [7 ]School of Chemistry
                [8 ]Cardiff University
                [9 ]Cardiff
                [10 ]UK
                [11 ]Department of Chemistry
                [12 ]University of Manitoba
                [13 ]Winnipeg
                [14 ]Canada
                [15 ]Duluth
                [16 ]USA
                Article
                DOI: 10.1039/C9CC04203B
                SO-VID: e0f1fa48-6540-4239-a596-57cc0f959f5d
                Copyright © © 2019
                License:

                Free to read

                http://rsc.li/journals-terms-of-use#chorus

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