Oxidative bromination of aniline and its derivatives

Salakhov, M. S.; Bağmanov, B. T.; Umaeva, V. S.; Bagmanova, M. I.

doi:10.1134/s1070427208080314

Cited by 8 publications

(5 citation statements)

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“…These zeolites have the added advantage of creating an acidic environment, meaning the less hazardous KBr can replace HBr as starting compound [37] . An alternative is to use a different acid, e. g. sulfuric acid, [37c,38] hydrochloric acid, [39] or p ‐toluenesulfonic acid, [40] to acidify the reaction mixture, or using a carboxylic acid, e. g. (trifluoro)acetic acid (TFA), as the solvent [41] . Although also an acid, acetic acid will act differently from the other acids mentioned.…”

Section: Peroxidesmentioning

confidence: 99%

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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: Peroxidesmentioning

confidence: 99%

“…Hydrogen peroxide has been successfully used to oxidatively brominate (di)ketones, [44,50] arenes, both through electrophilic ring bromination [35– 39,41b,45,48–,50d,51] and radical side‐chain bromination, [36,52] heteroarenes, [40,51b] and unsaturated bonds [28a,46,49– 50d,53] …”

Section: Peroxidesmentioning

confidence: 99%

Bromide Oxidation: A Safe Strategy for Electrophilic Brominations

2022

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“…Most of these methods are devoted to the generation of para-monobrominated products, − while others are dedicated to meta selectivity, and only a few result in ortho selectivity . There are very few reports that describe selectivity for tribrominated products. ,, Salakhov and co-workers obtained tribrominated products in high yields through oxidative bromination with KBr and hydrogen peroxide in HCl; however, they were unable to avoid the use of a hazardous protic acid. The use of TsNBr 2 (as the brominating agent) and organic solvents is a shortcomings of the method employed by Saikia and co-workers .…”

Section: Introductionmentioning

confidence: 99%

Graphene Oxide Promoted Oxidative Bromination of Anilines and Phenols in Water

2018

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The mildly acidic and oxidative nature of graphene oxide, with its large surface area available for catalytic activity, has been explored in aromatic nuclear bromination chemistry for the first time. The versatile catalytic activity of graphene oxide (GO) has been used to selectively and rapidly brominate anilines and phenols in water. The best results were obtained at ambient temperatures using molecular bromine in a protocol promoted by oxidative bromination catalyzed by GO; these transformations proceeded with 100% atom economy with respect to bromine and high selectivities for the tribromoanilines and -phenols. Reduced graphene oxide (r-GO) was observed to form after the second recycle (third use) of GO. This technique is also effective with N-bromosuccinimide (NBS) as the brominating reagent. In the case of NBS, reactions were instantaneous and the GO displayed excellent recyclability without any loss of activity over several cycles.

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“…. Также исследовано окислительное бромирование анилина и его производных, содержа-щих в о-, м-, п-положении различные заместители (CH 3 , Cl, NO 2 , COOH), и выявлено, что окислительное бромирование о-и п-замещенных анилинов отличается от бромирования м-замещенных производных и не зависит от электронной природы заместителей в фениль-ном кольце [23]. …”

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