Recent Advances in Bromination of Aromatic and Heteroaromatic Compounds

Voskressensky, Leonid G.; Голанцов, Никита Е.; Maharramov, Abel M.

doi:10.1055/s-0035-1561503

Cited by 66 publications

(35 citation statements)

References 108 publications

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“…A notable effort has been devoted towards the development of synthetic procedures for the preparation of aryl halides, particularly after the emergence of transition metal‐catalyzed coupling reactions, most of which require an aryl bromide as substrate . Although both nucleophilic and electrophilic bromination reactions are known, traditional approaches of nucleophilic bromination of arenes have limited substrate scopes and require harsh reaction conditions .…”

Section: Methodsmentioning

confidence: 99%

A Oxidative Bromination of (Hetero)Arenes in the TMSBr/DMSO System: A Non‐Aqueous Procedure Facilitates Synthetic Strategies

Kajita

Togni

2017

ChemistrySelect

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An oxidative bromination protocol for aromatic compounds using trimethylsilyl bromide (TMSBr) and DMSO has been developed. This mild bromination system tolerates a wide variety of functionalities including amide, aldehyde, ester and acetal groups. Arylbromides and heteroarylbromides are produced in up to 95 % yield at 25 °C. Arenes bearing electron‐donating groups are selectively brominated at the para position unless it is blocked. The highlight of this protocol consists in its non‐aqueous conditions, which are fruitful particularly in the context of integrated synthetic systems. The utility of this method was demonstrated with three examples, in either of which the bromination was followed by another reaction: a “click” triazole formation, a Suzuki–Miyaura cross‐coupling, or an aldehyde formation via lithium–bromine exchange, without the isolation of the bromide intermediate in any case. It is particularly remarkable for this non‐aqueous protocol to allow lithiation reactions to sequentially follow the bromination.

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Section: Methodsmentioning

confidence: 99%

A Oxidative Bromination of (Hetero)Arenes in the TMSBr/DMSO System: A Non‐Aqueous Procedure Facilitates Synthetic Strategies

Kajita

Togni

2017

ChemistrySelect

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“…We recently demonstrated that metal triflimide catalysis could be used to activate N ‐iodosuccinimide (NIS) for regioselective iodination of arenes and so a similar procedure was used to investigate bromination (Scheme ) . A mixture of iron(III) chloride (5 mol %) with the inexpensive ionic liquid 1‐butyl‐3‐methylimidazolium bis(trifluoromethylsulfonyl)imide ([BMIM]NTf 2 ), which forms the powerful Lewis acid Fe(NTf 2 ) 3 in situ, was found to activate N ‐bromosuccinimide (NBS) for the rapid and efficient bromination of a wide range of anisoles, phenols, anilines and acetanilides under mild conditions . Arenes with strongly deactivating groups (e.g., 1 l and 1 m ), naphthalenes ( 1 q and 1 r ) and 2,3‐benzodihydrofuran ( 1 s ) were all tolerated as substrates for effective bromination.…”

Section: Figurementioning

confidence: 99%

Intermolecular Aryl C−H Amination through Sequential Iron and Copper Catalysis

Mostafa

Calder

Racys

et al. 2016

Chemistry A European J

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A mild, efficient and regioselective method for para‐amination of activated arenes has been developed through a combination of iron and copper catalysis. A diverse range of products were obtained from an operationally simple one‐pot, two‐step procedure involving bromination of the aryl substrate with the powerful Lewis acid iron(III) triflimide, followed by a copper(I)‐catalysed N‐arylation reaction. This two‐step dehydrogenative process for the regioselective coupling of aromatic C−H bonds with non‐activated amines was applicable to anisole‐, phenol‐, aniline‐ and acetanilide‐type aryl compounds. Importantly, the arene substrates were used as the limiting reagent and required no protecting‐group manipulations during the transformation.

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“…Among many halogenating agents, CuBr 2 has been widely used in bromination and in other organic reactions . Contrasting with the great use of the free salt, few examples of bromination with CuBr 2 complexes are found in the literature .…”

Section: Introductionmentioning

confidence: 99%

Green Analysis of the Bromination Reaction of Propiophenone Derivatives Mediated by Cu²⁺ Complexes

Krapacher

Rossi

2020

ChemistrySelect

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All processes and reactions were evaluated using green metrics. Alternatives for the α-halogenation reaction of ketones were studied, varying both the methodology and the brominating reactants. CuBr 2 and its complexes with organic ligands derived from biomass were used as bromide source. Distinct regioselectivity and chemoselectivity were observed with the different complexes used. The CuBr 2 -βCD complex behave completely different to the rest of the complexes since the halogenation occurred preferentially in the propiophenone aromatic ring. Among the complexes used, novel starch and chitosan complexes with CuBr 2 were synthesized and characterized by EPR, FT-IR, UVV RD and TGA.

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Recent Advances in Bromination of Aromatic and Heteroaromatic Compounds

Abstract: This review covers recent advances in C-H bromination of aromatic substrates. Transition-metal-catalyzed/-mediated reactions and transition-metal-free methods are discussed.

Cited by 66 publications

References 108 publications

A Oxidative Bromination of (Hetero)Arenes in the TMSBr/DMSO System: A Non‐Aqueous Procedure Facilitates Synthetic Strategies

A Oxidative Bromination of (Hetero)Arenes in the TMSBr/DMSO System: A Non‐Aqueous Procedure Facilitates Synthetic Strategies

Intermolecular Aryl C−H Amination through Sequential Iron and Copper Catalysis

Green Analysis of the Bromination Reaction of Propiophenone Derivatives Mediated by Cu²⁺ Complexes

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Recent Advances in Bromination of Aromatic and Heteroaromatic Compounds

Abstract: This review covers recent advances in C-H bromination of aromatic substrates. Transition-metal-catalyzed/-mediated reactions and transition-metal-free methods are discussed.

Cited by 66 publications

References 108 publications

A Oxidative Bromination of (Hetero)Arenes in the TMSBr/DMSO System: A Non‐Aqueous Procedure Facilitates Synthetic Strategies

A Oxidative Bromination of (Hetero)Arenes in the TMSBr/DMSO System: A Non‐Aqueous Procedure Facilitates Synthetic Strategies

Intermolecular Aryl C−H Amination through Sequential Iron and Copper Catalysis

Green Analysis of the Bromination Reaction of Propiophenone Derivatives Mediated by Cu2+ Complexes

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Green Analysis of the Bromination Reaction of Propiophenone Derivatives Mediated by Cu²⁺ Complexes