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2-Iodobenzoic Acid

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Jarugu Narasimha Moorthy – One of the best experts on this subject based on the ideXlab platform.

  • Mechanochemical catalytic oxidations in the solid state with in situ-generated modified IBX from 3,5-di-tert-butyl-2-Iodobenzoic Acid (DTB-IA)/Oxone
    Organic Chemistry Frontiers, 2017
    Co-Authors: Abhaya Kumar Mishra, Jarugu Narasimha Moorthy

    Abstract:

    IBX is an indispensable reagent in contemporary organic oxidation chemistry, despite its explosive and insoluble attributes. The latter drawbacks can be overcome if a more reactive modified version of IBX can be generated in situ catalytically. We show that the sterically-crowded reactive I(V) species can be generated catalytically from the precursor 3,5-di-tert-butyl-2-Iodobenzoic Acid (DTB-IA) in the presence of a terminal oxidant, i.e., Oxone. The highly reactive modified IBX, i.e., I(V) species, generated in situ from DTB-IA in the presence of Oxone under mechanochemical ball milling conditions, permits unprecedented oxidation of alcohols to carbonyl compounds, vicinal diols to oxidative cleavage products, and non-vicinal diols to lactones in the solid state. Indeed, the results constitute first demonstration of catalytic oxidations in the solid state using a modified o-iodobenzoic Acid, an I(I) species.

  • Twist Does a Twist to the Reactivity: Stoichiometric
    and Catalytic Oxidations with Twisted Tetramethyl-IBX
    , 2016
    Co-Authors: Jarugu Narasimha Moorthy, Keshaba Nanda Parida, Kalyan Senapati, Samik Jhulki, Kunnikuruvan Sooraj, Nisanth N. Nair

    Abstract:

    The methyl groups in TetMe-IBX lower the activation energy
    corresponding
    to the rate-determining hypervalent twisting (theoretical
    calculations), and the steric relay between successive methyl groups twists the structure, which manifests in significant solubility
    in common organic solvents. Consequently, oxidations of alcohols and
    sulfides occur at room temperature in common organic solvents. In
    situ generation of the reactive TetMe-IBX from its
    precursor iodo-Acid, i.e., 3,4,5,6-tetramethyl-2-Iodobenzoic Acid,
    in the presence of oxone as a co-oxidant facilitates the oxidation
    of diverse alcohols at room temperature

  • Oxidative cleavage of olefins by in situ-generated catalytic 3,4,5,6-tetramethyl-2-iodoxybenzoic Acid/oxone.
    Journal of Organic Chemistry, 2014
    Co-Authors: Jarugu Narasimha Moorthy, Keshaba Nanda Parida

    Abstract:

    Oxidative cleavage of a variety of olefins to the corresponding ketones/carboxylic Acids is shown to occur in a facile manner with 3,4,5,6-tetramethyl-2-Iodobenzoic Acid (TetMe-IA)/oxone. The simple methodology involves mere stirring of the olefin and catalytic amount (10 mol %) of TetMe-IA and oxone in acetonitrile–water mixture (1:1, v/v) at rt. The reaction mechanism involves initial dihydroxylation of the olefin with oxone, oxidative cleavage by the in situ-generated 3,4,5,6-tetramethyl-2-iodoxybenzoic Acid (TetMe-IBX), and oxidation of the aldehyde functionality to the corresponding Acid with oxone. Differences in the reactivities of electron-rich and electron-poor double bonds have been exploited to demonstrate chemoselective oxidative cleavage in substrates containing two double bonds.

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

  • Preparation, Structure, and Reactivity of Pseudocyclic Benziodoxole Tosylates: New Hypervalent Iodine Oxidants and Electrophiles
    Chemistry (Weinheim an der Bergstrasse Germany), 2016
    Co-Authors: Akira Yoshimura, Khiem C Nguyen, Gregory T Rohde, Akio Saito, Mekhman S Yusubov, Scott C. Klasen, Pavel S. Postnikov, Victor N. Nemykin, Michael T. Shea, Viktor V Zhdankin

    Abstract:

    New pseudocyclic benziodoxole tosylates were prepared by the treatment of 1-hydroxybenziodoxolones with p-toluenesulfonic Acid or via ligand transfer reaction between PhI(OH)OTs (Koser’s reagent) and substituted 2-Iodobenzoic Acids under mild condition. Single crystal X-ray crystallography of these compounds revealed a pseudocyclic structure with a short intramolecular interaction of 2.362(3) A between oxygen and iodine in the iodoxole ring. Pseudocyclic benziodoxole tosylates readily react with various organic substrates as electrophiles or oxidants to afford the corresponding iodonium salts or the products of oxidation. Furthermore, these compounds can be used as efficient recyclable hypervalent iodine reagents. The reduced form of a pseudocyclic benziodoxole tosylate, 2-Iodobenzoic Acid, can be efficiently recovered from the reaction mixture by a simple Acid-base liquid-liquid biphasic procedure.

  • oxidative cycloaddition of aldoximes with maleimides using catalytic hydroxy aryl iodonium species
    Advanced Synthesis & Catalysis, 2016
    Co-Authors: Akira Yoshimura, Khiem C Nguyen, Gregory T Rohde, Akio Saito, Mekhman S Yusubov, Viktor V Zhdankin

    Abstract:

    A mild catalytic procedure for the efficient oxidative cyclization of aldoximes with maleimides mediated by hypervalent iodine(III) active species has been developed. This catalytic cyclization affords the corresponding pyrrolo-isoxazole products in generally good yields. The catalytic cycle involves active hydroxy(aryl)iodonium species generated in situ from 2-Iodobenzoic Acid as precatalyst and m-chloroperoxybenzoic Acid (m-CPBA) as terminal oxidant in the presence of trifluoromethanesulfonic Acid. The presence of active hydroxy(aryl)iodonium species in this reaction has been confirmed by ESI-mass spectrometry and 1H NMR spectroscopy.

  • oxidative cycloaddition of aldoximes with maleimides using catalytic hydroxy aryl iodonium species
    Advanced Synthesis & Catalysis, 2016
    Co-Authors: Akira Yoshimura, Khiem C Nguyen, Gregory T Rohde, Akio Saito, Mekhman S Yusubov, Viktor V Zhdankin

    Abstract:

    A mild catalytic procedure for the efficient oxidative cyclization of aldoximes with maleimides mediated by hypervalent iodine(III) active species has been developed. This catalytic cyclization affords the corresponding pyrrolo-isoxazole products in generally good yields. The catalytic cycle involves active hydroxy(aryl)iodonium species generated in situ from 2-Iodobenzoic Acid as precatalyst and m-chloroperoxybenzoic Acid (m-CPBA) as terminal oxidant in the presence of trifluoromethanesulfonic Acid. The presence of active hydroxy(aryl)iodonium species in this reaction has been confirmed by ESI-mass spectrometry and 1H NMR spectroscopy.

Keshaba Nanda Parida – One of the best experts on this subject based on the ideXlab platform.

  • Twist Does a Twist to the Reactivity: Stoichiometric
    and Catalytic Oxidations with Twisted Tetramethyl-IBX
    , 2016
    Co-Authors: Jarugu Narasimha Moorthy, Keshaba Nanda Parida, Kalyan Senapati, Samik Jhulki, Kunnikuruvan Sooraj, Nisanth N. Nair

    Abstract:

    The methyl groups in TetMe-IBX lower the activation energy
    corresponding
    to the rate-determining hypervalent twisting (theoretical
    calculations), and the steric relay between successive methyl groups twists the structure, which manifests in significant solubility
    in common organic solvents. Consequently, oxidations of alcohols and
    sulfides occur at room temperature in common organic solvents. In
    situ generation of the reactive TetMe-IBX from its
    precursor iodo-Acid, i.e., 3,4,5,6-tetramethyl-2-Iodobenzoic Acid,
    in the presence of oxone as a co-oxidant facilitates the oxidation
    of diverse alcohols at room temperature

  • Oxidative cleavage of olefins by in situ-generated catalytic 3,4,5,6-tetramethyl-2-iodoxybenzoic Acid/oxone.
    Journal of Organic Chemistry, 2014
    Co-Authors: Jarugu Narasimha Moorthy, Keshaba Nanda Parida

    Abstract:

    Oxidative cleavage of a variety of olefins to the corresponding ketones/carboxylic Acids is shown to occur in a facile manner with 3,4,5,6-tetramethyl-2-Iodobenzoic Acid (TetMe-IA)/oxone. The simple methodology involves mere stirring of the olefin and catalytic amount (10 mol %) of TetMe-IA and oxone in acetonitrile–water mixture (1:1, v/v) at rt. The reaction mechanism involves initial dihydroxylation of the olefin with oxone, oxidative cleavage by the in situ-generated 3,4,5,6-tetramethyl-2-iodoxybenzoic Acid (TetMe-IBX), and oxidation of the aldehyde functionality to the corresponding Acid with oxone. Differences in the reactivities of electron-rich and electron-poor double bonds have been exploited to demonstrate chemoselective oxidative cleavage in substrates containing two double bonds.

  • Oxidative Cleavage of Olefins
    by In Situ-Generated
    Catalytic 3,4,5,6-Tetramethyl-2-iodoxybenzoic Acid/Oxone
    , 2014
    Co-Authors: Jarugu Narasimha Moorthy, Keshaba Nanda Parida

    Abstract:

    Oxidative
    cleavage of a variety of olefins to the corresponding
    ketones/carboxylic Acids is shown to occur in a facile manner with
    3,4,5,6-tetramethyl-2-Iodobenzoic Acid (TetMe-IA)/oxone. The simple
    methodology involves mere stirring of the olefin and catalytic amount
    (10 mol %) of TetMe-IA and oxone in acetonitrile–water mixture
    (1:1, v/v) at rt. The reaction mechanism involves initial dihydroxylation
    of the olefin with oxone, oxidative cleavage by the in situ-generated
    3,4,5,6-tetramethyl-2-iodoxybenzoic Acid (TetMe-IBX), and oxidation
    of the aldehyde functionality to the corresponding Acid with oxone.
    Differences in the reactivities of electron-rich and electron-poor
    double bonds have been exploited to demonstrate chemoselective oxidative
    cleavage in substrates containing two double bonds