N-Bromosuccinimide in Acetonitrile: A Mild and Regiospecific Nuclear Brominating Reagent for Methoxybenzenes and Naphthalenes

Carreño, M. Carmen; Ruano, José Luis Garcı́a; Sanz, Gema; Toledo, Miguel Ángel; Urbano, Antonio

doi:10.1021/jo00121a064

Cited by 183 publications

(121 citation statements)

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“…Attempted bromination of 15 with Br 2 in CHCl 3 was ineffective even after 24 h at 100 °C, and the reaction between 15 and NBS in acetonitrile 58 yielded a mixture of products. In addition to the desired C-H brominated product, GC/MS analysis indicated products where resulting from C-BPin scission.…”

Section: Synthetic Elaborations Of Borylated Thiophenesmentioning

confidence: 99%

“…The product was extracted with CH 2 Cl 2 (3 × 20 mL) and dried over MgSO 4 General procedure D (substitution of TMS with Br): TMS group were replaced with bromine by employing the literature conditions used for aromatic C-H bromination. 58 Substrate (1 mmol, 1 equiv) was added to a 20 mL scintillation vial equipped with a magnetic stirring bar. N-Bromosuccinamide (1 mmol, 1 equiv) was added in to the vial.…”

Section: -Methyl-5-(3-(trifluoromethyl)phenyl)thiophene (25)mentioning

confidence: 99%

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Iridium-catalyzed borylation of thiophenes: versatile, synthetic elaboration founded on selective C–H functionalization

et al. 2008

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Iridium-catalyzed borylation has been applied to various substituted thiophenes to synthesize polyfunctionalized thiophenes in good to excellent yields. Apart from common functionalities compatible with iridium-catalyzed borylations, additional functional group tolerance to acyl (COMe), and trimethylsilyl (TMS) groups was also observed. High regioselectivities were observed in borylation of 3-and 2,5-di-substituted thiophenes. Electrophilic aromatic C-H/C-Si bromination on thiophene boronate esters is shown to take place without breaking the C-B bond, and one-pot C-H borylation/Suzuki-Miyaura cross-coupling has been accomplished on 2-and 3-borylated thiophenes.

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Section: Synthetic Elaborations Of Borylated Thiophenesmentioning

confidence: 99%

Section: -Methyl-5-(3-(trifluoromethyl)phenyl)thiophene (25)mentioning

confidence: 99%

Iridium-catalyzed borylation of thiophenes: versatile, synthetic elaboration founded on selective C–H functionalization

et al. 2008

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“…[14][15][16]. Some side reactions maybe occurred during the process of polymerization because NBS is a highly regioselective bromination reagent [9,10]. The methine in the polystyrene adjacent to the benzene ring reacted with NBS and the succinimide was produced, which decreased the concentration of initiator and some graft polymers may be produced [17,18] as depicted in Scheme 1 (Eq.…”

Section: Resultsmentioning

confidence: 99%

“…As a mild and regiospecific brominating reagent, N-bromosuccinimide (NBS) was used in Wohl-Ziegler reactions and many functional substances were synthesized [8][9][10]. The latter, such as α-haloesters, α-haloketones, α-halonitriles and α-haloamides, may be employed as initiators in ATRP.…”

Section: Introductionmentioning

confidence: 99%

Atom transfer radical polymerization of styrene initiated by the novel initiator N-bromosuccinimide

Zhang

Zhu

2004

E-Polymers

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Heterogeneous atom transfer radical polymerization of styrene initiated by N-bromosuccinimide in bulk was successfully carried out with CuBr/2,2'-bipyridine as the catalyst. The kinetics follow first order in monomer and molecular weights (polydispersities M w /M n = 1.23 -1.66) increase linearly with monomer conversion, indicating the 'living'/controlled nature of the polymerization. However, the number-average molecular weights were usually higher than the theoretical ones. That demonstrates the relatively low efficiency of the initiator, the causes of which are discussed. The obtained polystyrenes functionalized with α-α-pyrrolidine-2,5-dionyl and ω-Br as the end groups were characterized by 1 H NMR spectroscopy. They can be used as macroinitiators for chain extension reaction. A polymerization mechanism for this novel initiation system is proposed.

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“…[7] The nuclear bromination of activated aromatic systems with NBS is generally favored in polar solvents such as propylene carbonate, DMF and CH 3 CN. [8] However, the use of solvents like water, supercritical fluids and ionic liquids has recently received a great deal of attention in different areas of organic chemistry.…”

Section: Introductionmentioning

confidence: 99%

Efficient Halogenation of Aromatic Systems Using N‐Halosuccinimides in Ionic Liquids

Yadav

Reddy

et al. 2004

Adv Synth Catal

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A simple, rapid and highly regioselective green protocol has been developed for the halogenation of aromatic systems with N-halosuccinimides using room temperature ionic liquids (ILs) as novel and recyclable reaction media to produce the corresponding halogenated aromatic compounds in high to quantitative yields. N-Halosuccinimides show enhanced reactivity in ionic liquids thereby reducing the reaction times dramatically and improving the yields substantially.

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N-Bromosuccinimide in Acetonitrile: A Mild and Regiospecific Nuclear Brominating Reagent for Methoxybenzenes and Naphthalenes

Cited by 183 publications

References 0 publications

Iridium-catalyzed borylation of thiophenes: versatile, synthetic elaboration founded on selective C–H functionalization

Iridium-catalyzed borylation of thiophenes: versatile, synthetic elaboration founded on selective C–H functionalization

Atom transfer radical polymerization of styrene initiated by the novel initiator N-bromosuccinimide

Efficient Halogenation of Aromatic Systems Using N‐Halosuccinimides in Ionic Liquids

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