A User-Friendly Entry to 2-Iodoxybenzoic Acid (IBX)

Frigerio, M.; Santagostino, and Marco; Sputore, Simona

doi:10.1021/jo9824596

Cited by 649 publications

(420 citation statements)

References 14 publications

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“…39 (salen)], were prepared as described in the cited references. Dimethyldioxirane 42 and iodoxybenzoic acid 43 were prepared according to published procedures.…”

Section: Methodsmentioning

confidence: 99%

Oxidation of mono-phenols to para-benzoquinones: a comparative study

Uliana¹,

Vieira²,

Donatoni³

et al. 2008

J. Braz. Chem. Soc.

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A oxidação de mono-fenóis à para-benzoquinonas é assunto de interesse contínuo devido à existência de inúmeros produtos naturais contendo esta unidade estrutural. As para-benzoquinonas possuem reatividade química importante como agentes oxidantes e como dienófilos na reação de Diels-Alder. Usualmente nós preparamos as para-benzoquinonas pela reação de oxidação dos respectivos mono-fenóis com oxigênio molecular e catalisada por [Co II (salen)]. Porém, foi necessário estudar estas oxidações utilizando-se outros oxidantes. Nós apresentamos aqui nossos resultados sobre esta importante reação de oxidação com uma variedade de oxidantes, utilizando onze mono-fenóis como substratos. Os oxidantes utilizados foram cobalto, níquel, cobre e vanádio derivados com alguns ligantes do tipo salen. Também foram estudados peróxido de hidrogênio, OXONE®, dimetil dioxirano e ácido iodoxibenzóico.The oxidation of mono-phenols to para-benzoquinones is of continuing interest due to the existence of numerous natural products containing this structural unit. The chemical reactivity of para-benzoquinones is also noteworthy, as oxidants and dienophiles in the Diels-Alder reaction. We have used for quite some time now, molecular oxygen and catalysis with [Co II (salen)] as the oxidation procedure, but felt the need for other oxidants and conditions to be of use with different phenol substrates. We now present our results on this important oxidation with a variety of oxidants, using eleven mono-phenols as substrates. The oxidants tested are cobalt, nickel, copper and vanadyl metals, with a selection of different salen type ligands. Completing this study we also investigated the use of hydrogen peroxide, OXONE®, dimethyl dioxirane and iodoxybenzoic acid. Keywords: oxidation, alkyl-substituted phenols, para-benzoquinones IntroductionNatural products frequently occur containing the parabenzoquinone sub-structural unit within the global structure, as can be exemplified by vitamins K 1 and K 2 , co-enzyme Q (ubiquinone), 1 and in many terpenes and alkaloids. 2 These natural products 3-13 are associated with important biological properties, such as cardiovascular, anti-tumour, antibacterial, anti-germination and anti-protozoan among others. There is no doubt that the para-benzoquinone nucleus is an important charge transfer receptor and easily undergoes nucleophilic addition reactions. 1 The redox relation with para-hydroquinones (para-quinols) is of importance in biological activity, and also makes many simple para-benzoquinones excellent oxidizing agents. 1 Synthetically, the para-benzoquinone structural unit is an excellent dienophile for the Diels-Alder reaction, among other relevant reactions. 1 The usual and obvious manner to prepare parabenzoquinones 1,14,15 is from the corresponding parahydroquinones, which is however rather limited due to the lack of a wide range of commercially or synthetically available substrates. As a second choice, the simple monophenol is an ideal substrate due to the ready availability of an extremely wide range of...

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“…39 (salen)], were prepared as described in the cited references. Dimethyldioxirane 42 and iodoxybenzoic acid 43 were prepared according to published procedures.…”

Section: Methodsmentioning

confidence: 99%

Oxidation of mono-phenols to para-benzoquinones: a comparative study

Uliana¹,

Vieira²,

Donatoni³

et al. 2008

J. Braz. Chem. Soc.

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“…The IBX reagent 215 was synthesised from 2-iodobenzoic acid and oxone in water using a procedure reported by Santagostino, Scheme 42. [268] IBX made by this method is proposed to pose much less of an explosion risk compared with that synthesised using potassium bromate. [266,269] Using the Santagostino method, pure IBX was isolated as a precipitate from the reaction in a moderate 76 % yield.…”

Section: Synthetic Route Twomentioning

confidence: 99%

“…[268] 2-iodobenzoic acid ( [305] Trimethyl-(4-phenylselanylphenylethynyl)silane 217 nBuLi (2.5 M in hexane, 0.13 mL, 0.33 mmol, 0.95 eq.) was added dropwise to a stirred solution of diisopropylamine …”

Section: -Iodoxybenzoic Acid 215 and 1-hydroxy-12-benziodoxol-3(1h)mentioning

confidence: 99%

Kinetic Template‐Guided Tethering of Fragments

2012

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This thesis is composed of two separate projects: Kinetic Template-Guided Tethering of Fragments and Design and Synthesis of a Chemical Probe to Dissect the Cellular Signalling Cascade leading to Cyclin D1 Degradation after DNA Damage. Kinetic Template-Guided Tethering of FragmentsThe development of a novel methodology for the site-directed discovery of small molecule, protein-binding ligands is described. The protein of interest, with a cysteine thiol (either native or engineered) adjacent to the desired binding pocket, is incubated with mixtures of low molecular weight compounds (fragments) modified with either an acrylamide or a vinyl sulfonamide capture group. Any ligand within the mixture that binds within the pocket brings the capture group into close proximity with the cysteine thiol, promoting a conjugate addition reaction at an increased rate over the background reaction. The capture reaction is designed to be slow, such that during the time course of an experiment, no adduct formation is observed unless the reaction is templated by the protein. By this method, binding ligands are rapidly identified by mass spectrometry analysis of the crude reaction mixtures. The methodology has been termed 'kinetic template-guided tethering'. Design and Synthesis of a Chemical Probe to Dissect the Cellular Signalling Cascade leading to Cyclin D1Degradation after DNA Damage An inhibitor described within the literature was found to attenuate the reduction of cyclin D1 after DNA damage to cells. In order to implement a two-step chemical proteomics strategy to find the molecular target of this inhibitor, a synthesis of the compound with an alkyne appendage was required. The alkyne acts as a functional handle for attachment of a reporter molecule in cells via the Huisgen cycloaddition ('Click') reaction. The design and synthesis of this inhibitor with the alkyne appendage is described.

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“…This linker was subsequently coupled to aminopropylsilica gel with DIC/HOBt to give compound 6. Cleavage of the tert-butylester with trifluoroacetic acid and oxidation with oxone 18 afforded the final reagent 7.…”

Section: Issn 1551-7012mentioning

confidence: 99%

“…[1][2][3][4][5][6] They can be used for a wide range of chemical transformations, especially as reagents for oxidations. [7][8][9][10][11] For these purposes, iodinanes like (diacetoxyiodo)-benzene,…”

Section: Introductionmentioning

confidence: 99%

First synthesis and oxidative properties of polymer-supported IBX

Mülbaier¹,

Giannis²

2003

Arkivoc

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A polymer-supported analogue of the IBX-reagent (1-hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide) has been synthesized. Synthesis and oxidative properties of this new and efficient reagent are described. With this reagent is it now possible to oxidize alcohols selectively to the corresponding ketones and aldehydes. Over oxidation to carboxylic acids has not been observed. This new reagent combines the advantages of polymer-supported reagents with those of the IBX reagent.

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A User-Friendly Entry to 2-Iodoxybenzoic Acid (IBX)

Abstract: IBX, 1-hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide (2iodoxybenzoic acid 1), has been known for more than a century, although its presence on the scene of organic synthesis has remained limited primarily due to its remarkable insolubility in most organic solvents. 1,2b,3a

Cited by 649 publications

References 14 publications

Oxidation of mono-phenols to para-benzoquinones: a comparative study

Oxidation of mono-phenols to para-benzoquinones: a comparative study

Kinetic Template‐Guided Tethering of Fragments

First synthesis and oxidative properties of polymer-supported IBX

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