Bromination of Deactivated Aromatics: A Simple and Efficient Method

Rajesh, K.; Somasundaram, M.; Saiganesh, R.; Balasubramanian, K. K.

doi:10.1021/jo070477u

Cited by 78 publications

(36 citation statements)

References 39 publications

(27 reference statements)

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“…Among these reagents, N-bromosuccinimide (NBS) is a useful brominating reagent in laboratory synthesis, since only inert succinimide by-product formed in the process. A lot of methods have been developed for the preparation of aryl bromides from electron-rich aromatics, but the bromination of unactivated aromatics with NBS proceeded only in the presence of stoichiometric amounts of strong Lewis acids or protic acids as catalysts [7][8][9][10]. Moreover, harsh experimental conditions were required for the bromination of deactivated aromatics, such as high temperature and high acidic solutions [11,12].…”

Section: Introductionmentioning

confidence: 99%

Silver Catalyzed Bromination of Aromatics with N-bromosuccinimide

et al. 2012

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Section: Introductionmentioning

confidence: 99%

Silver Catalyzed Bromination of Aromatics with N-bromosuccinimide

et al. 2012

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“…There are several halogenation methods available in literatures. [18][19][20][21][22][23] Some of the methods [18][19][20][21][22] were tried and did not introduce halogen only into the phenyl ring A of the final molecule PF-622. Krishna and her coworkers 23 reported that an aniline and anisole can be brominated by the electrophilic substitution of bromine-generated in situ from ammonium bromide as a bromine source and hydrogen peroxide as an oxidant.…”

Section: Resultsmentioning

confidence: 99%

Preparation of tritium‐labeled PF‐622, a novel fatty acid amide hydrolase inhibitor

Zhang

2017

Labelled Comp Radiopharmac

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To make a detailed characterization of the mechanism of inhibition and selectivity of a novel fatty acid amide hydrolase inhibitor PF-622, 3 tritium isotopomers were prepared. [ H]PF-622a labeled at the piperazine ring B and [ H]PF-622b labeled at both the ring B and phenyl ring A were synthesized via catalytic H(hydrogen)-T(tritium) exchange, utilizing 1 equiv and excess of Crabtree's catalyst, respectively. The preparation of [ H]PF-622c labeled only at the phenyl ring A was achieved via tritiodebromination of the bromide precursor, using Pd(PPh ) as a catalyst. The observations from these tritiation reactions might open a new perspective in the labeling for the targets having a similar moiety.

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“…This compound was prepared in four steps by bromination of 3-nitrobenzoic acid (12), [25] reduction of the carboxylic acid, [26] protection of the resulting alcohol as a MOM ether, [27] and a Bechamp reduction of the nitro group (Scheme 6). [28] The overall yield was 61 % over four steps.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Isomerization Studies of Cyclotrisazobiphenyl

Reuter

Wegner

2011

Chemistry A European J

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We report an efficient synthesis of cyclotris[(E)-3'-(biphenyl-3-yldiazenyl)] compounds (CTBs). An unsubstituted CTB molecule is accessible in four steps in 10% yield overall, whereas a hexa(methoxymethyl ether) CTB analogue was prepared in nine steps (26% yield). The final macrocyclization step was accomplished in up to 80% yield by using a metal-template effect. Furthermore, the photochromic properties were investigated, and all four isomers were detected and characterized by NMR spectroscopy. A strong influence from the solvent and the irradiation wavelength on the switching process was observed. Irradiation in pyridine yielded the highest amount of the all-Z isomer in the photostationary state. For a full conversion to the all-E isomer, the reaction has to be heated to 45 °C. The isomerization to the all-E isomer is slow at room temperature, with a half-life time of the all-Z isomer of more than nine days in dimethyl sulfoxide (DMSO). Conditions were established to access each possible isomer as the major component in the photostationary state.

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Bromination of Deactivated Aromatics: A Simple and Efficient Method

Cited by 78 publications

References 39 publications

Silver Catalyzed Bromination of Aromatics with N-bromosuccinimide

Silver Catalyzed Bromination of Aromatics with N-bromosuccinimide

Preparation of tritium‐labeled PF‐622, a novel fatty acid amide hydrolase inhibitor

Synthesis and Isomerization Studies of Cyclotrisazobiphenyl

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