A Green Protocol for the Bromination and Iodination of the Aromatic Compounds using H5IO6/NaBr and H5IO6/NaI in the Water

Seyf, Jaber Yousefi; Tajeian, Kazem; Kolvari, Eskandar; Koukabi, Nadiya; Khazaei, Ardeshir

doi:10.5012/bkcs.2012.33.8.2619

Cited by 15 publications

(4 citation statements)

References 29 publications

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“…The only article describing the use of iodate to oxidatively brominate aromatics was by Khazaei et al ., who obtained, apart from statistically insignificant variation, identical results as their previous article performing identical reactions; however, using sodium periodate instead of sodium iodate [141–142] . Later, periodate and iodate were compared with the equivalent iodination [138c] …”

Section: Sodium Periodatesupporting

confidence: 51%

Bromide Oxidation: A Safe Strategy for Electrophilic Brominations

2022

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Bromination of organic substances is still an important reaction in modern synthetic chemistry. In view of the increasing demand for sustainable synthetic chemistry, oxidative bromination can play an important role to avoid the use of hazardous molecular bromine (Br 2 ). In this review, a complete overview of the chemical oxidants will be provided which have been used for the electrophilic as well as radical brominations, starting from less hazardous bromide Br(À I); e. g., HBr or a bromide salt, with a focus on the differences caused by the choice of oxidant.

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Section: Sodium Periodatesupporting

confidence: 51%

Bromide Oxidation: A Safe Strategy for Electrophilic Brominations

2022

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“…One of the most effective solutions to this situation is the use of iodonium equivalents (I + ), for example, N-iodosuccinimide, [7] Niodosaccharin, [8] iodine monochloride [9] and IOAc. [10] Another effective solution is the oxidative activation strategy where the electrophilic I + -type species is generated through oxidation of iodine sources by oxidizing reagent systems, for example, CrO 3 , [11] PbA C H T U N G T R E N N U N G (OAc) 4 , [12] CeA C H T U N G T R E N N U N G (OTf) 4 , [13] hydrogen peroxide, [14] H 5 IO 6 , [15] peroxodisulfate salts, [16] and ferrate salts. [17] The use of molecular oxygen as the oxidant is a still desirable goal from environmental and economic perspectives.…”

Section: Introductionmentioning

confidence: 99%

Nitrogen Dioxide‐Catalyzed Electrophilic Iodination of Arenes

et al. 2013

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Nitrogen dioxide is demonstrated to be an effective catalyst precursor for the iodination of alkoxy-substituted benzenes and naphthalenes. Different from the transition metal catalysts, nitrogen dioxide can be easily separated from the final products, and is free of heavy metal waste. Although the present catalyst precursor is toxic, it does not stain the final products due to its low-boiling character. No other reagents apart from 0.5 equiv. of iodine (I 2 ), 6.5 mol% nitrogen dioxide and acetonitrile solvent were used in the iodination, and basically all the iodine atoms in the iodine source were transferred to the iodination products, showing that the presented protocol is highly atom-economic and practical.

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“…Hou J. et al have reported [10] about an ecologically safe method of bromination of 4-nitroaniline (scheme 6) at room temperature, by use of the I2O5KBr water system. The bromination of aromatic amines in CH2Cl2/H2O with HJO3/KBr [11] and in water with ortho-periodic acid / sodium bromide (1: 2) (scheme 7) [12] has been carried out at room temperature for a short time. The bromination of various substituted anilines with oxone and sodium bromide (scheme 8) has been carried out [13] while stirring at room temperature, solutions of anilines, oxone and sodium bromide in 1:1 mixture of CH3CN/H2O.…”

Section: Scheme 4 схема 4 Scheme 5 схемаmentioning

confidence: 99%

Bromination of Aromatic Amines

Mustafayeva

Kakhramanov

2019

IVKKT

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It is known that the antipyrenes, biological active substances (antitumor, antibacterial, antifungal, antiviral), pharmacological preparations on the basis of bromine-containing aromatic compounds are widely used in the industry. Considering this and increased demand for these substances the purpose of this work was to summarize and systematize the accumulated knowledge in this area. The article presents methods and reagent systems used in the bromination of aromatic amines. There have been described the bromination of aromatic amines with hydrogen bromide, sodium bromide, potassium bromide, ammonium bromide, copper (II) bromide, N-bromosuccinimide, N-bromosaccharin, polymer-supported halogenation agents, and difference of these methods from the point of view of the used oxidizer, the medium and the solvent, the catalyst, the regioselectivity, the quantity of bromine atoms in the obtained product. The influence of solvents, catalysts, the nature (electron-donor or electron-acceptor) and position (ortho-, meta-, para-) of the substituents in the aromatic ring, reaction conditions, molar ratio of the reagents, reaction temperature and carrying out time of bromination reaction of aromatic amines has been shown. The bromination reactions courses of aromatic amines in different solvents, in solvent free conditions, in solid states has been described. The bromination of aromatic amines under thermal, microwave, ultraviolet radiation conditions has been studied. In the paper the regioselective monobromination and also obtaining of di-, tri- bromo derivatives of aromatic amines has been shown. Taking into account today's priority to environmentally safe methods of bromination of aromatic amines they have been also mentioned. Given the above, in our opinion, the information presented in this article will help to optimize the production of bromo derivatives of aromatic amines used in industry, technics and technology.

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A Green Protocol for the Bromination and Iodination of the Aromatic Compounds using H₅IO₆/NaBr and H₅IO₆/NaI in the Water

Cited by 15 publications

References 29 publications

Bromide Oxidation: A Safe Strategy for Electrophilic Brominations

Bromide Oxidation: A Safe Strategy for Electrophilic Brominations

Nitrogen Dioxide‐Catalyzed Electrophilic Iodination of Arenes

Bromination of Aromatic Amines

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