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Halogenation of Alkenes02:46

Halogenation of Alkenes

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Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
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Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

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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...
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Reactions at the Benzylic Position: Halogenation01:11

Reactions at the Benzylic Position: Halogenation

4.0K
Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
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Nucleophilic Aromatic Substitution: Elimination–Addition01:11

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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...
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Base-Promoted α-Halogenation of Aldehydes and Ketones00:51

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α-Halogenation of aldehydes and ketones is a reaction involving the substitution of α hydrogens with halogens in the presence of a base.  The reaction begins with the abstraction of  α hydrogen by the base to produce a nucleophilic enolate ion. This intermediate undergoes a subsequent nucleophilic substitution with the halogen to produce a monohalogenated carbonyl compound. If the starting substrate has more than one α hydrogen, it is difficult to stop the reaction...
4.4K
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

8.0K
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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Selective Halogenation Using an Aniline Catalyst.

Ramesh C Samanta1, Hisashi Yamamoto2

  • 1Molecular Catalyst Research Center, Chubu University, 1200 Matsumoto, Kasugai, Aichi 487-8501 (Japan). rsamanta@isc.chubu.ac.jp.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|July 18, 2015
PubMed
Summary

This study introduces a novel catalytic method for electrophilic halogenation using N-halo arylamine intermediates. This approach offers a selective and efficient way to synthesize various halogenated aromatic and heteroaromatic compounds.

Keywords:
aniline catalystaromatic compoundshalo-cyclizationhalogenationheteroaromatic compounds

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Halogenation Reactions

Background:

  • Electrophilic halogenation is crucial for synthesizing halogenated compounds.
  • Existing methods primarily rely on stoichiometric reagents.
  • A catalytic approach for halogen transfer remains a significant challenge.

Purpose of the Study:

  • To develop a novel catalytic system for electrophilic halogenation.
  • To utilize N-halo arylamine intermediates as catalytic electrophilic halogen sources.
  • To achieve selective halogenation of aromatic and heteroaromatic compounds.

Main Methods:

  • Arylamines were employed to generate N-halo arylamine intermediates.
  • Commercially available N-halosuccinimides (NCS, NBS, NIS) were used as halogen sources.
  • The catalytic system was applied to various aromatic and heteroaromatic substrates.

Main Results:

  • The N-halo arylamine intermediate demonstrated high reactivity and selectivity.
  • Good to excellent yields were obtained for a wide range of compounds.
  • Specific outcomes included allylic chlorides from unactivated double bonds and bromocyclization for polyolefins.
  • Catalyst reactivity was tunable by modifying the electronic properties of the arene moiety.

Conclusions:

  • A new catalytic method for electrophilic halogenation has been successfully developed.
  • The N-halo arylamine intermediate serves as an effective catalytic halogen source.
  • This method provides a versatile and selective route to halogenated organic molecules.