Regioselective Aromatic Electrophilic Bromination with Dioxane Dibromide Under Solvent‐Free Conditions

Chaudhuri, Subrata Kumar; Roy, Swapnila; Saha, M.; Bhar, Sanjay

doi:10.1080/00397910601055081

Cited by 16 publications

(7 citation statements)

References 9 publications

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“…However, at room temperature, a considerable amount of ortho isomer formation was observed. A more detailed study of this protocol was later taken up by Bhar et al , They found that this solvent-free protocol is highly regioselective for aromatic electrophilic bromination (Scheme ). Notable features of this methodology include operational simplicity, rapid reactions, excellent control over the degree of bromination, and tolerance of various functional groups during the reaction.…”

Section: Bromination Reactionsmentioning

confidence: 99%

“…A more detailed study of this protocol was later taken up by Bhar et al , They found that this solvent-free protocol is highly regioselective for aromatic electrophilic bromination (Scheme ). Notable features of this methodology include operational simplicity, rapid reactions, excellent control over the degree of bromination, and tolerance of various functional groups during the reaction. They also found that phenol and anisole were not overbrominated beyond 2,4-dibromo derivatives despite the use of an excess amount of dioxane dibromide.…”

Section: Bromination Reactionsmentioning

confidence: 99%

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Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

2016

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Bromination is one of the most important transformations in organic synthesis and can be carried out using bromine and many other bromo compounds. Use of molecular bromine in organic synthesis is well-known. However, due to the hazardous nature of bromine, enormous growth has been witnessed in the past several decades for the development of solid bromine carriers. This review outlines the use of bromine and different bromo-organic compounds in organic synthesis. The applications of bromine, a total of 107 bromo-organic compounds, 11 other brominating agents, and a few natural bromine sources were incorporated. The scope of these reagents for various organic transformations such as bromination, cohalogenation, oxidation, cyclization, ring-opening reactions, substitution, rearrangement, hydrolysis, catalysis, etc. has been described briefly to highlight important aspects of the bromo-organic compounds in organic synthesis.

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Section: Bromination Reactionsmentioning

confidence: 99%

Section: Bromination Reactionsmentioning

confidence: 99%

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

2016

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“…1 In addition, regioselective nuclear bromination of activated aromatic and heteroaromatic compounds can also be performed by means of N-bromosuccinimide with tetrabutylammonium bromide present as a phase-transfer catalyst 2 or using dioxane dibromide. 3 Selective monobromination of electron-rich arenes has also been reported using CuBr 2 4 or alkali metal bromides in the presence of concentrated H 2 SO 4 5 or various oxidants, 6 sometimes in the presence of acids 7 and/or catalysts. 8 Several of these methods are, however, saddled with various drawbacks making them environmentally unfriendly and unsuitable for large-scale industrial use due to (1) low atom economy as the large N-succinimide molecular fragment is used as the bromine carrier, (2) the requirement of auxiliary reagents, (3) toxic solvents as the reaction medium, and (4) harsh reaction conditions.…”

Section: Introductionmentioning

confidence: 97%

A novel simple and efficient bromination protocol for activated arenes

Tsoukala

Liguori²,

Occhipinti

et al. 2009

Tetrahedron Letters

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“…A plethora of information is available for the bromination of unprotected anilines and phenols. 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.…”

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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Regioselective Aromatic Electrophilic Bromination with Dioxane Dibromide Under Solvent‐Free Conditions

Cited by 16 publications

References 9 publications

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

A novel simple and efficient bromination protocol for activated arenes

Graphene Oxide Promoted Oxidative Bromination of Anilines and Phenols in Water

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