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Related Concept Videos

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

6.5K
Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
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Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

8.8K
Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
8.8K
Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

5.5K
In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
5.5K
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

4.1K
Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
4.1K
α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction

3.2K
The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the...
3.2K
Reactions at the Benzylic Position: Halogenation01:11

Reactions at the Benzylic Position: Halogenation

2.8K
Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
2.8K

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Related Experiment Video

Updated: Sep 20, 2025

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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Olefin-Catalyzed Aromatic Bromination toward Biocompatible Tyrosine Modification.

Riku Sakaguchi1, Takuto Shimazu1, Rakuto Yoshida2

  • 1Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigaku-Katsura, Nishikyo, Kyoto, 615-8510, Japan.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|May 27, 2025
PubMed
Summary

Researchers developed a new catalytic method for aromatic bromination using cyclic olefins. This technique enables efficient tyrosine modification under mild, aqueous conditions, advancing biomolecular labeling strategies.

Keywords:
aromatic brominationbiocompatibilitylight‐gated catalystolefintyrosine modification

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Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
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Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
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Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry

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Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
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Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry

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Area of Science:

  • Chemical Biology
  • Organic Chemistry
  • Biomolecular Engineering

Background:

  • Chemical modification of biomolecules is key to understanding biological processes.
  • Catalysis offers advantages in selectivity and control over stoichiometric methods.
  • Tyrosine modification is significant due to its biological roles, but selective bromination is challenging under physiological conditions.

Purpose of the Study:

  • To develop a catalyst-controlled aromatic bromination method under near-physiological conditions.
  • To enable efficient and selective tyrosine bromination for biomolecular labeling.
  • To create a light-activated catalytic system for in situ modification.

Main Methods:

  • Developed catalytic aromatic bromination using in-situ generated bromiranium ions from cyclic olefins.
  • Employed bifunctional cyclooctenes with a hydroxybenzyl group as catalysts.
  • Investigated substituent effects on catalyst generation rates and kinetics.
  • Demonstrated light-gated catalysis via photochemical deprotection.

Main Results:

  • Efficient bromination of phenol derivatives and tyrosine residues was achieved.
  • Catalysis was compatible with aqueous conditions, enabling peptide modification.
  • Light-activated catalysis allowed for spatiotemporal control of bromination.
  • The method demonstrated Lewis-base catalysis even under acidic conditions.

Conclusions:

  • Developed a novel olefin-based catalytic system for aromatic bromination.
  • The method provides a biocompatible and efficient approach for tyrosine modification.
  • The light-gated capability offers precise control for in situ biomolecular labeling.