Practical Synthesis of 2-Iodosobenzoic Acid (IBA) without Contamination by Hazardous 2-Iodoxybenzoic Acid (IBX) under Mild Conditions

China, Hideyasu; Kageyama, N.; Yatabe, H.; Takenaga, Naoko; Dohi, Toshifumi

doi:10.3390/molecules26071897

Cited by 4 publications

(2 citation statements)

References 114 publications

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“…Various aryl carboxylates successfully incorporated into α‐acyloxy sulfides from the substituted BI−OMe derivatives, which could be easily prepared from o ‐iodobenzoic acid derivatives (Table 3). [12b,17] The electron‐rich methoxy or electron‐withdrawing halides, nitriles, and trifluoromethyl groups at the meta ‐position were all tolerated on the substituted BI−OMe derivatives, afforded 28 – 35 in 58–88% yields. Notably, the 5‐nitro‐2‐iodobenzoic acid gave 31 in 88% yield with a prolonged 12 h reaction time [18] .…”

Section: Methodsmentioning

confidence: 99%

Selective C−H Acyloxylation of Sulfides/Disulfides Enabled by Hypervalent Iodine Reagents

Chen

2023

Adv Synth Catal

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Herein, we report the α−C−H acyloxylation of sulfides and disulfides enabled by hypervalent iodine(III) reagents via photoredox catalysis. The methoxylbenziodoxole derivatives serve as the hydrogen atom transfer agent, the mild oxidant, and the acyloxylation source in the reaction. External nucleophiles can also be introduced to the α−C−H of sulfides. The reaction applies to various aryl and alkyl sulfides including methionine peptide derivatives. Disulfides are applicable for the first time with excellent chemoselectivity and functional group compatibility.magnified image

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Section: Methodsmentioning

confidence: 99%

Selective C−H Acyloxylation of Sulfides/Disulfides Enabled by Hypervalent Iodine Reagents

Chen

2023

Adv Synth Catal

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“…Thus, the coupling reaction in the presence of 1-acetoxy-1,2-benziodoxol-3(1 H )-one, a hypervalent iodine reagent with a cyclic structure, afforded a high yield (88%) of 3a , without peroxidation (entry 5). Furthermore, 1-acetoxy-5-fluoro-1,2-benziodoxol-3(1 H )-one, − bearing the electron-withdrawing group fluorine, demonstrated improved reactivity, increasing the yield to 92% (entry 6). Iodine reagents bearing electron-donating groups like methoxy groups (entry 7), and those bearing bromo groups that have low solubility (entry 8), decreased the product yield .…”

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confidence: 99%

Cyclic Hypervalent Iodine-Induced Oxidative Phenol and Aniline Couplings with Phenothiazines

et al. 2022

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C−H/N−H bond functionalization for direct intermolecular aryl C−N couplings is a useful synthetic process. In this study, we achieved metal-free cross-dehydrogenative coupling of phenols and anilines with phenothiazines using hypervalent iodine reagents. This method affords selective amination products under mild conditions. Electron-rich phenols and anilines could be employed, affording moderate-to-high yields of N-arylphenothiazines. Aniline amination proceeded efficiently at 20 °C, a previously unreported phenomenon.

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Amino‐ and Alkoxybenziodoxoles: Facile Preparation and Use as Arynophiles

Kanemoto,

Yoshimura,

Ono

et al. 2024

Chemistry A European J

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We report here on the facile synthesis of amino‐ and alkoxy‐λ3‐iodanes supported by a benziodoxole (BX) template and their use as arynophiles. The amino‐ and alkoxy‐BX derivatives can be readily synthesized by reacting the respective amines or alcohols with chlorobenziodoxole in the presence of a suitable base. Unlike previously known nitrogen‐ and oxygen‐bound iodane compounds, which have primarily been employed as electrophilic group transfer agents or oxidants, the present amino‐ and alkoxy‐BX reagents manifest themselves as nucleophilic amino and alkoxy transfer agents toward arynes. This reactivity leads to the aryne insertion into the N–I(III) or O–I(III) bond to afford ortho‐amino‐ and ortho‐alkoxyarylbenziodoxoles, iodane compounds nontrivial to procure by existing methods. The BX group in these insertion products exhibits excellent leaving group ability, enabling diverse downstream transformations.

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Practical Synthesis of 2-Iodosobenzoic Acid (IBA) without Contamination by Hazardous 2-Iodoxybenzoic Acid (IBX) under Mild Conditions

Cited by 4 publications

References 114 publications

Selective C−H Acyloxylation of Sulfides/Disulfides Enabled by Hypervalent Iodine Reagents

Selective C−H Acyloxylation of Sulfides/Disulfides Enabled by Hypervalent Iodine Reagents

Cyclic Hypervalent Iodine-Induced Oxidative Phenol and Aniline Couplings with Phenothiazines

Amino‐ and Alkoxybenziodoxoles: Facile Preparation and Use as Arynophiles

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