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2-Iodoxybenzoic Acid

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Viktor V. Zhdankin – One of the best experts on this subject based on the ideXlab platform.

  • Benziodoxole-Derived Organosulfonates: The Strongest Hypervalent Iodine Electrophiles and Oxidants
    Synlett, 2019
    Co-Authors: Mekhman S. Yusubov, Akira Yoshimura, Pavel Postnikov, Viktor V. Zhdankin

    Abstract:

    This account describes the development of organosulfonyloxy-substituted iodine(III) and iodine(V) benziodoxole derived reagents, which are thermally stable compounds with useful reactivity patterns. Iodine(III) benziodoxoles and pseudobenziodoxoles are powerful electrophiles and mild oxidants toward various unsaturated compounds. In particular, pseudocyclic benziodoxole-derived triflate (IBA-OTf) is an efficient reagent for oxidative heteroannulation reactions. Aldoximes react with nitriles in the presence of IBA-OTf at room temperature to give 1,2,4-oxadiazoles in high yields. Moreover, IBA-triflate is used as a catalyst in oxidative heteroannulations with m-chloroperoxybenzoic Acid as the terminal oxidant. The iodine(V) benziodoxole derived tosylates, DMP-tosylate and IBX-tosylate, are superior oxidants for the oxidation of structurally diverse, synthetically useful alcohols, utilized as key precursors in the total syntheses of polyketide antibiotics and terpenes. And finally, the most powerful hypervalent iodine(V) oxidant, 2-Iodoxybenzoic Acid ditriflate (IBX·2HOTf), is prepared by treatment of IBX with trifluoromethanesulfonic Acid. According to the X-ray data, the I–OTf bonds in IBX-ditriflate have ionic character, leading to the high reactivity of this reagent in various oxidations. In particular, IBX-ditriflate can oxidize polyfluorinated primary alcohols, which are generally extremely resistant to oxidation.1 Introduction2 Iodine(III) Benziodoxole Based Organosulfonates3 Pseudocyclic Iodine(III) Benziodoxole Triflate (IBA-triflate)4 Pseudocyclic Iodine(III) Benziodoxole Tosylates5 Iodine(V) Benziodoxole Derived Tosylates6 Iodine(V) Benziodoxole Derived Triflate (IBX-ditriflate)7 Conclusions

  • 2-Iodoxybenzoic Acid ditriflate: the most powerful hypervalent iodine(V) oxidant
    Chemical Communications, 2019
    Co-Authors: Mekhman S. Yusubov, Natalia S. Soldatova, Pavel S. Postnikov, Rashid R. Valiev, Akira Yoshimura, Thomas Wirth, Victor N. Nemykin, Viktor V. Zhdankin

    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.

  • 2-Iodoxybenzoic Acid Tosylates: the Alternative to Dess–Martin Periodinane Oxidizing Reagents
    Advanced Synthesis & Catalysis, 2017
    Co-Authors: Mekhman S. Yusubov, Pavel S. Postnikov, Akira Yoshimura, Roza Ya. Yusubova, Gerrit Jürjens, Andreas Kirschning, Viktor V. Zhdankin

    Abstract:

    Two powerful hypervalent iodine(V) oxidants, DMP-OTs (1-tosyloxy-1,1-diacetoxy-1H-1λ5-benzo[d][1,2]iodoxol-3-one) and IBX-OTs (1-tosyloxy-1-oxo-1H-1λ5-benzo[d][1,2]iodoxol-3-one) show high reactivity in the oxidation of structurally complex primary and secondary alcohols, which are highly functionalized polyketide or terpene fragments or steroids. The yields of the corresponding carbonyl compounds are even higher for the protocol that uses pyridine as additive. The oxidations proceed very rapidly at room temperature leaving the protective groups and π-systems intact and affording the corresponding carbonyl compounds in good to excellent yields. Moreover, IBX-OTs is an efficient reagent for the oxidative dehydrogenation of steroidal alcohols to the corresponding enones.

Q.a Wang – One of the best experts on this subject based on the ideXlab platform.

  • Controllable and efficient oxidation of thioether by 2-Iodoxybenzoic Acid (IBX) in water: Semisynthesis of sophocarpine
    Tetrahedron Letters, 2014
    Co-Authors: Chaojie Li, Yuxiu Liu, Q.a Wang

    Abstract:

    A metal-free, environment friendly, easy-to-operate, and efficient method for the semisynthesis of sophocarpine from matrine has been developed in an overall yield of 91%. The route features a controllable and efficient oxidation of thioether to sulfoxide by 2-Iodoxybenzoic Acid (IBX) in water. ?? 2014 Elsevier Ltd. All rights reserved.

Chaojie Li – One of the best experts on this subject based on the ideXlab platform.

  • Controllable and efficient oxidation of thioether by 2-Iodoxybenzoic Acid (IBX) in water: semisynthesis of sophocarpine
    Tetrahedron Letters, 2014
    Co-Authors: Chaojie Li, Qingmin Wang

    Abstract:

    A metal-free, environment friendly, easy-to-operate, and efficient method for the semisynthesis of sophocarpine from matrine has been developed in an overall yield of 91%. The route features a controllable and efficient oxidation of thioether to sulfoxide by 2-Iodoxybenzoic Acid (IBX) in water.

  • Controllable and efficient oxidation of thioether by 2-Iodoxybenzoic Acid (IBX) in water: Semisynthesis of sophocarpine
    Tetrahedron Letters, 2014
    Co-Authors: Chaojie Li, Yuxiu Liu, Q.a Wang

    Abstract:

    A metal-free, environment friendly, easy-to-operate, and efficient method for the semisynthesis of sophocarpine from matrine has been developed in an overall yield of 91%. The route features a controllable and efficient oxidation of thioether to sulfoxide by 2-Iodoxybenzoic Acid (IBX) in water. ?? 2014 Elsevier Ltd. All rights reserved.