131-62-4

Usage

Uses

Used in Organic Synthesis:
1-Hydroxy-2-oxa-1-ioda(III)indan-3-one is used as a terminal oxidant for gold-catalyzed, three-component oxyarylation reactions. It plays a crucial role in facilitating the formation of desired products by promoting selective oxidation processes.
Used in Catalyst Synthesis:
1-Hydroxy-2-oxa-1-ioda(III)indan-3-one is employed as a catalyst in the synthesis of ynones via a hypervalent iodine-catalyzed reaction. Its unique structure and reactivity enable it to efficiently catalyze the formation of ynones, which are valuable building blocks in organic chemistry.

InChI:InChI=1/C7H5IO3/c9-7-5-3-1-2-4-6(5)8(10)11-7/h1-4,10H

Upstream product

• 615-37-2 ortho-methylphenyl iodide 
• 88-67-5 2-Iodobenzoic acid 
• 1829-26-1 1-acetoxy-1,2-benziodoxol-3-one 
• 115479-51-1 2-Iodo-benzoic acid 2,3-bis-octanoyloxy-propyl ester 
• 155791-59-6 Phosphoric acid 3-oxo-3H-1λ³-benzo[d][1,2]iodoxol-1-yl ester diphenyl ester 
• 15753-50-1 cis-1,2-cyclohexanedimethanol 
• 61717-82-6 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione 
• 185566-81-8 1-Methoxy-1-oxo-1H-1λ⁵-benzo[d][1,2]iodoxol-3-one 
• 185566-82-9 1-Ethoxy-1-oxo-1H-1λ⁵-benzo[d][1,2]iodoxol-3-one 
• 142260-70-6 1-(tert-butylperoxy)-1,2-benziodoxol-3(1H)-one 
• 1493-13-6 trifluorormethanesulfonic acid 
• 610-97-9 o-iodo-methyl-benzoic acid 
• 160732-56-9 1-azido-1λ³-benzo[d][1,2]iodaoxol-3(1H)-one 
• 591-50-4 iodobenzene 

Downstream Products

• 1829-26-1 1-acetoxy-1,2-benziodoxol-3-one 
• 142260-70-6 1-(tert-butylperoxy)-1,2-benziodoxol-3(1H)-one 
• 131251-55-3 2-iodo-3-(2-propynyl)benzoic acid 
• 135226-07-2 1-(cyclohexylethynyl)-1,2-benziodoxol-3(1H)-one 
• 159950-96-6 1-(p-methylbenzenesulfonyloxy)-1,2-benziodoxol-3(1H)-one 
• 164268-27-3 1-hexynyl-(o-carboxyphenyl)iodonium triflate 
• 164268-31-9 phenylethynyl(o-carboxyphenyl)iodonium triflate 
• 172876-96-9 3-oxo-1λ³-benzo[d][1,2]iodaoxole-1(3H)-carbonitrile 
• 108981-92-6 2-(naphthalene-1-yl)benzoic acid 
• 18110-71-9 4'-methoxybiphenyl-2-carboxylic acid 
• 7148-03-0 o-tolylbenzoic acid 
• 7111-77-5 2'-methyl[1,1'-biphenyl]-carboxylic acid 
• 947-84-2 2-Biphenylcarboxylic acid 
• 186298-88-4 4-Chloro-N-(3-oxo-3H-1λ³-benzo[d][1,2]iodoxol-1-yl)-benzamide 

Relevant academic research and scientific papers

Photoredox Imino Functionalizations of Olefins

Shown herein is that polyfunctionalized nitrogen heterocycles can be easily prepared by a visible-light-mediated radical cascade process. This divergent strategy features the oxidative generation of iminyl radicals and subsequent cyclization/radical trapping, which allows the effective construction of highly functionalized heterocycles. The reactions proceed efficiently at room temperature, utilize an organic photocatalyst, use simple and readily available materials, and generate, in a single step, valuable building blocks that would be difficult to prepare by other methods.

Regio- and Stereoselective Iron-Catalyzed Oxyazidation of Enamides Using a Hypervalent Iodine Reagent

A novel regio- and diastereoselective iron-catalyzed intermolecular oxyazidation of enamides using various azidobenziodoxolone (ABX) derivatives is presented. A variety of α-N3 amino derivatives and of α-N3 piperidines were synthesized in good yields and under mild reaction conditions. The reaction involves a radical process using cheap FeCl2 as the initiator.

Enantioselective Synthesis of Homoallylic Azides and Nitriles via Palladium-Catalyzed Decarboxylative Allylation

Azides and nitriles are important building blocks for the synthesis of nitrogen-containing bioactive compounds. The first example of enantioselective palladium-catalyzed decarboxylative allylation of α-azido and cyano β-ketoesters is reported. Indanone derivatives were obtained in 50-88% yield/77-97% ee and 46-98% yield/78-93% ee for azide and nitrile substituents, respectively. The required starting materials were synthesized in one step from ketoesters via electrophilic azidation and cyanation using benziodoxole hypervalent iodine reagents. The products could be easily converted into useful nitrogen-containing building blocks, such as triazoles, amides, or α- and β- amino ketones.

Practical synthesis of 2-iodosobenzoic acid (IBA) without contamination by hazardous 2-iodoxybenzoic acid (IBX) under mild conditions

We report a convenient and practical method for the preparation of nonexplosive cyclic hypervalent iodine(III) oxidants as efficient organocatalysts and reagents for various reactions using Oxone in aqueous solution under mild conditions at room temperature. The thus obtained 2-iodosobenzoic acids (IBAs) could be used as precursors of other cyclic organoiodine(III) derivatives by the solvolytic derivatization of the hydroxy group under mild conditions of 80 °C or lower temperature. These sequential procedures are highly reliable to selectively afford cyclic hypervalent iodine compounds in excellent yields without contamination by hazardous pentavalent iodine(III) compound.

Ethynylation of Cysteine Residues: From Peptides to Proteins in Vitro and in Living Cells

Current approaches to introduce terminal alkynes for bioorthogonal reactions into biomolecules still present limitations in terms of either reactivity, selectivity, or adduct stability. We present a method for the ethynylation of cysteine residues based on the use of ethynylbenziodoxolone (EBX) reagents. The acetylene group is directly introduced onto the thiol group of cysteine and can be used for copper-catalyzed alkyne-azide cycloaddition (CuAAC) without further processing. Labeling proceeded with reaction rates comparable to or higher than the most often used iodoacetamide on peptides or maleimide on the antibody trastuzumab, and high cysteine selectivity was observed. The reagents were also used in living cells for cysteine proteomic profiling and displayed improved coverage of the cysteinome compared to previously reported iodoacetamide or hypervalent iodine reagents. Fine-tuning of the EBX reagents allows optimization of their reactivity and physical properties.

Oxidative Cycloaddition of Aldoximes with Maleimides using Catalytic Hydroxy(aryl)iodonium Species

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 and1H NMR spectroscopy. (Figure presented.) .

The direct electrophilic cyanation of β-keto esters and amides with cyano benziodoxole

The direct electrophilic α-cyanation of β-keto esters and amides has been developed using a hypervalent iodine benziodoxole-derived cyano reagent. The procedure is accomplished within 10 min and without the use of any catalyst in DMF, at room temperature. Thus, the highly functionalized quaternary carbon-centered nitriles were produced in high to excellent yields.

Enantioenriched Quaternary α-Pentafluoroethyl Derivatives of Alkyl 1-Indanone-2-Carboxylates

An electrophilic enantioselective catalytic method for the α-pentafluoroethylation of 3-oxoesters is described. Under the use of La(OTf)3 in combination with a (S,R)-indanyl-pybox ligand, good results in terms of yield and enantioselectivities were achieved (up to 89% ee). The reaction proceeds under mild conditions, leading to the formation of enantioenriched quaternary centers. This methodology uses an hypervalent iodine(III)-CF2CF3 reagent, and mechanistic investigations are consistent with the involvement of a radical pathway.

Thermal stability of N-heterocycle-stabilized iodanes-A systematic investigation

The thermal stability of pseudocyclic and cyclic N-heterocycle-stabilized (hydroxy)aryl-and mesityl(aryl)-λ3-iodanes (NHIs) through thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC) is investigated. Peak decomposition temperatures (Tpeak) were observed within a wide range between 120 and 270 °C. Decomposition enthalpies (ΔHdec) varied from-29.81 to 141.13 kJ/mol. A direct comparison between pseudocyclic and cyclic NHIs revealed high Tpeak but also higher ΔHdec values for the latter ones. NHIs bearing N-heterocycles with a high N/C-ratio such as triazoles show among the lowest Tpeak and the highest ΔHdec values. A comparison of NHIs with known (pseudo)cyclic benziodoxolones is made and we further correlated their thermal stability with reactivity in a model oxygenation.

Preparation, structure, and unexpected chemistry of phosphoranyl-derived benziodoxoles

Novel phosphoranyl-derived benziodoxoles were prepared by the reaction of 1-acetoxybenziodoxole with stabilized phosphonium ylides [1-triphenylphosphoranylidene-2-propanone and (carbomethoxymethyl)triphenylphosphoranylidene acetate]. X-ray crystallographic analysis of these compounds demonstrates the significance of secondary bonding interactions, which link individual molecules into infinite chains. An unusual ligand exchange on an iodine(III) center resulting in the substitution of a carbon ligand with an oxygen ligand was observed in the reaction of these compounds with strong acids. Copyright