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Jarugu Narasimha Moorthy - One of the best experts on this subject based on the ideXlab platform.
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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, 2017Co-Authors: Abhaya Kumar Mishra, Jarugu Narasimha MoorthyAbstract: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.
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Twist Does a Twist to the Reactivity: Stoichiometric and Catalytic Oxidations with Twisted Tetramethyl-IBX
2016Co-Authors: Jarugu Narasimha Moorthy, Keshaba Nanda Parida, Kalyan Senapati, Samik Jhulki, Kunnikuruvan Sooraj, Nisanth N. NairAbstract: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
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Oxidative cleavage of olefins by in situ-generated catalytic 3,4,5,6-tetramethyl-2-iodoxybenzoic Acid/oxone.
Journal of Organic Chemistry, 2014Co-Authors: Jarugu Narasimha Moorthy, Keshaba Nanda ParidaAbstract: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.
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Oxidative Cleavage of Olefins by In Situ-Generated Catalytic 3,4,5,6-Tetramethyl-2-iodoxybenzoic Acid/Oxone
2014Co-Authors: Jarugu Narasimha Moorthy, Keshaba Nanda ParidaAbstract: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
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Twist Does a Twist to the Reactivity: Stoichiometric and Catalytic Oxidations with Twisted Tetramethyl-IBX
The Journal of organic chemistry, 2011Co-Authors: Jarugu Narasimha Moorthy, Keshaba Nanda Parida, Kalyan Senapati, Samik Jhulki, Kunnikuruvan Sooraj, Nisanth N. NairAbstract: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.
Viktor V Zhdankin - One of the best experts on this subject based on the ideXlab platform.
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Preparation, Structure, and Reactivity of Pseudocyclic Benziodoxole Tosylates: New Hypervalent Iodine Oxidants and Electrophiles
Chemistry (Weinheim an der Bergstrasse Germany), 2016Co-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 ZhdankinAbstract: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.
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oxidative cycloaddition of aldoximes with maleimides using catalytic hydroxy aryl iodonium species
Advanced Synthesis & Catalysis, 2016Co-Authors: Akira Yoshimura, Khiem C Nguyen, Gregory T Rohde, Akio Saito, Mekhman S Yusubov, Viktor V ZhdankinAbstract: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.
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oxidative cycloaddition of aldoximes with maleimides using catalytic hydroxy aryl iodonium species
Advanced Synthesis & Catalysis, 2016Co-Authors: Akira Yoshimura, Khiem C Nguyen, Gregory T Rohde, Akio Saito, Mekhman S Yusubov, Viktor V ZhdankinAbstract: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.
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Hypervalent Iodine‐Catalyzed Synthesis of 1,2,4‐Oxadiazoles from Aldoximes and Nitriles
Asian Journal of Organic Chemistry, 2016Co-Authors: Akira Yoshimura, Khiem C Nguyen, Akio Saito, Mekhman S Yusubov, Scott C. Klasen, Pavel S. Postnikov, Victor N. Nemykin, Viktor V ZhdankinAbstract:A convenient procedure for oxidative cycloaddition of aldoximes with nitriles using stoichiometric or catalytic amounts of hypervalent iodine(III) reagent IBA-OTf (2-iodosylbenzoic Acid triflate) has been developed. This efficient procedure works well for the preparation of various 1,2,4-oxadiazoles in generally high yields under mild reaction conditions. The actual oxidant in this reaction, IBA-OTf, is prepared from 2-iodosylbenzoic Acid (IBA) and trifluoromethanesulfonic Acid (TfOH) or it can be generated in situ from 2-Iodobenzoic Acid and m-chloroperoxybenzoic Acid (m-CPBA) in the presence of TfOH. The nature of hydroxy(aryl)iodonium species, generated in situ from 2-Iodobenzoic Acid, m-CPBA, and TfOH under catalytic reaction conditions, has been confirmed by 1H NMR spectroscopy, ESI-mass spectrometry, and by X-ray diffraction.
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Preparation and X-ray structural study of 1-arylbenziodoxolones.
The Journal of organic chemistry, 2013Co-Authors: Mekhman S Yusubov, Victor N. Nemykin, Roza Ya. Yusubova, Viktor V ZhdankinAbstract:Various 1-arylbenziodoxolones can be conveniently prepared from 2-Iodobenzoic Acid and arenes by a one-pot procedure using Oxone (2KHSO5·KHSO4·K2SO4) as an inexpensive and environmentally safe oxidant. This procedure is also applicable for the synthesis of the 7-methylbenziodoxolone ring system using 2-iodo-3-methylbenzoic Acid as starting compound. Structures of four 1-arylbenziodoxolone derivatives were established by single-crystal X-ray diffraction analysis. An enhanced reactivity of 1-aryl-7-methylbenziodoxolones toward nucleophiles compared to unsubstituted 1-arylbenziodoxolones has been found.
Keshaba Nanda Parida - One of the best experts on this subject based on the ideXlab platform.
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Twist Does a Twist to the Reactivity: Stoichiometric and Catalytic Oxidations with Twisted Tetramethyl-IBX
2016Co-Authors: Jarugu Narasimha Moorthy, Keshaba Nanda Parida, Kalyan Senapati, Samik Jhulki, Kunnikuruvan Sooraj, Nisanth N. NairAbstract: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
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Oxidative cleavage of olefins by in situ-generated catalytic 3,4,5,6-tetramethyl-2-iodoxybenzoic Acid/oxone.
Journal of Organic Chemistry, 2014Co-Authors: Jarugu Narasimha Moorthy, Keshaba Nanda ParidaAbstract: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.
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Oxidative Cleavage of Olefins by In Situ-Generated Catalytic 3,4,5,6-Tetramethyl-2-iodoxybenzoic Acid/Oxone
2014Co-Authors: Jarugu Narasimha Moorthy, Keshaba Nanda ParidaAbstract: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
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Twist Does a Twist to the Reactivity: Stoichiometric and Catalytic Oxidations with Twisted Tetramethyl-IBX
The Journal of organic chemistry, 2011Co-Authors: Jarugu Narasimha Moorthy, Keshaba Nanda Parida, Kalyan Senapati, Samik Jhulki, Kunnikuruvan Sooraj, Nisanth N. NairAbstract: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.
Thottumkara K. Vinod - One of the best experts on this subject based on the ideXlab platform.
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In situ Generation of o‐Iodoxybenzoic Acid (IBX) and the Catalytic Use of It in Oxidation Reactions in the Presence of Oxone as a Co‐oxidant.
ChemInform, 2005Co-Authors: Arun P. Thottumkara, Bowsher Michael S, Thottumkara K. VinodAbstract:[structure: see text] Catalytic use of o-iodoxybenzoic Acid (IBX) in the presence of Oxone as a co-oxidant is demonstrated for the oxidation of primary and secondary alcohols in user- and eco-friendly solvent mixtures. Also demonstrated is the in situ (re)oxidation of 2-iodosobenzoic Acid (IBA) and even commercially available 2-Iodobenzoic Acid (2IBAcid) by Oxone to IBX allowing one to use these less hazardous reagents, in place of potentially explosive IBX, as catalytic oxidants.
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In situ generation of o-iodoxybenzoic Acid (IBX) and the catalytic use of it in oxidation reactions in the presence of Oxone as a co-oxidant.
Organic letters, 2005Co-Authors: Arun P. Thottumkara, Bowsher Michael S, Thottumkara K. VinodAbstract:Catalytic use of o-iodoxybenzoic Acid (IBX) in the presence of Oxone as a co-oxidant is demonstrated for the oxidation of primary and secondary alcohols in user- and eco-friendly solvent mixtures. Also demonstrated is the in situ (re)oxidation of 2-iodosobenzoic Acid (IBA) and even commercially available 2-Iodobenzoic Acid (2IBAcid) by Oxone to IBX allowing one to use these less hazardous reagents, in place of potentially explosive IBX, as catalytic oxidants.
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In situ generation of o-iodoxybenzoic Acid (IBX) and the catalytic use of it in oxidation reactions in the presence of Oxone as a co-oxidant.
Organic letters, 2005Co-Authors: Arun P. Thottumkara, Bowsher Michael S, Thottumkara K. VinodAbstract:[structure: see text] Catalytic use of o-iodoxybenzoic Acid (IBX) in the presence of Oxone as a co-oxidant is demonstrated for the oxidation of primary and secondary alcohols in user- and eco-friendly solvent mixtures. Also demonstrated is the in situ (re)oxidation of 2-iodosobenzoic Acid (IBA) and even commercially available 2-Iodobenzoic Acid (2IBAcid) by Oxone to IBX allowing one to use these less hazardous reagents, in place of potentially explosive IBX, as catalytic oxidants.
Michael J. Mckenzie - One of the best experts on this subject based on the ideXlab platform.
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In Situ Generation of 2-Iodoxybenzoic Acid (IBX) in the Presence of Tetraphenylphosphonium Monoperoxysulfate (TPPP) for the Conversion of Primary Alcohols into the Corresponding Aldehydes
Synlett, 2007Co-Authors: Philip C. Bulman Page, Louise F. Appleby, Steven M. Allin, Benjamin R. Buckley, Michael J. MckenzieAbstract:Primary alcohols are oxidized to the corresponding aldehydes by tetraphenylphosphonium monoperoxysul fate (TPPP) in the presence of catalytic 2-Iodobenzoic Acid, Overoxidation to carboxylic Acids is not observed, in contrast to the use of catalytic 2-Iodobenzoic Acid with Oxone (R) as reoxidant.