Expedient synthesis and solvent dependent oxidation behavior of a water-soluble IBX derivative

Kommreddy, Amitha; Bowsher, Michael S.; Gunna, Meena R.; Botha, Kirankumar; Vinod, Thottumkara K.

doi:10.1016/j.tetlet.2008.05.017

Cited by 47 publications

(24 citation statements)

References 25 publications

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“…When dissolved in aqueous DMF, 8 displayed reactivity similar to that of IBX towards alcohols. [34] However, the reaction does not proceed as cleanly in other aqueous solvent mixtures. Tetrafluoro-IBX (9, FIBX) was developed by Wirth and co-workers and seems to hold even greater synthetic potential.…”

Section: Alexandermentioning

confidence: 99%

2‐Iodoxybenzoic Acid—A Simple Oxidant with a Dazzling Array of Potential Applications

2011

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Since its discovery by Christoph Hartmann and Victor Meyer in 1893, 2-iodoxybenzoic acid (IBX) has emerged as a rather ubiquitous oxidant for organic synthesis. The past decade has seen the development of a large variety of applications that go far beyond the simple oxidation of alcohols. This Review is concerned with the synthetic potential of IBX, with particular emphasis on uncommon reactivity patterns and novel fields of application.

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Section: Alexandermentioning

confidence: 99%

2‐Iodoxybenzoic Acid—A Simple Oxidant with a Dazzling Array of Potential Applications

2011

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“…Elemental analysis was provided by Atlantic Microlab, Norcross, GA. High resolution mass spectrometry (HRMS) data was provided by the Mass Spectrometry and Proteomics facility at the Ohio State University. The preparation of iodoterephthalic acid ( 5 ) has been reported in literature , but the method used in this study is entirely different and the experimental protocol is therefore provided. Full experimental details on the preparation and spectroscopic characterization of compounds 1 , 3 , and 10 are reported in a recent publication .…”

Section: Methodsmentioning

confidence: 99%

Structure, Theoretical Studies, and Coupling Reactions of Some New Cyclic Boronic Esters

Kuttler

Durganala

Fratini

et al. 2013

Heteroatom Chemistry

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The present report describes the X‐ray structural and theoretical studies of some new pinacolboronate esters, and it also outlines the use of the target structures in Suzuki coupling reactions to produce new aromatic or heteroaromatic esters and amides. X‐ray structural analysis of the studied compounds revealed that the pinacolborane ring's position with respect to the benzene ring varies, depending on the particular environment. An ortho‐positioned carboxylic ester (methyl ester) causes a nearly perpendicular orientation of the pinacolborane unit with respect to the benzene ring, whereas an ortho‐positioned amide (N,N‐dimethylamide) causes the pinacolborane unit to orient itself nearly coplanar. A plausible explanation has been provided, based on both steric and electronic factors.

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“…[33] Eine etwas größere Anwendungsbreite zeigte das Isomer 8, das in wässrigem DMF ähnliche Reaktivität bezüglich der Oxidation von Alkoholen besitzt wie IBX. [34] In anderen wässrigen Lösungsmittelge-mischen verläuft die Reaktion allerdings weniger sauber. Deutlich größeres Synthesepotenzial verspricht das von Wirth et al entwickelte Tetrafluor-IBX (9, FIBX).…”

Section: Derivate Von Ibx Und Deren Anwendung In Der Syntheseunclassified

2‐Iodoxybenzoesäure – ein einfaches Oxidationsmittel mit einer Vielfalt an Anwendungsmöglichkeiten

Duschek

Kirsch

2011

Angewandte Chemie

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Seit seiner Entdeckung durch Christoph Hartmann und Victor Meyer im Jahr 1893 hat sich 2‐Iodoxybenzoesäure (IBX) zu einem geradezu ubiquitär einsetzbaren Oxidationsmittel entwickelt. Insbesondere in den vergangenen zehn Jahren wurde eine Vielzahl von Anwendungsmöglichkeiten beschrieben, die weit über die einfache Oxidation von Alkoholen hinausgehen. Dieser Aufsatz behandelt das Potenzial von IBX in der Synthese, wobei insbesondere unerwartete Reaktivitäten und moderne Anwendungen im Mittelpunkt der Diskussion stehen.

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Expedient synthesis and solvent dependent oxidation behavior of a water-soluble IBX derivative

Cited by 47 publications

References 25 publications

2‐Iodoxybenzoic Acid—A Simple Oxidant with a Dazzling Array of Potential Applications

2‐Iodoxybenzoic Acid—A Simple Oxidant with a Dazzling Array of Potential Applications

Structure, Theoretical Studies, and Coupling Reactions of Some New Cyclic Boronic Esters

2‐Iodoxybenzoesäure – ein einfaches Oxidationsmittel mit einer Vielfalt an Anwendungsmöglichkeiten

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