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Related Concept Videos

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

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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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Reactions at the Benzylic Position: Halogenation01:11

Reactions at the Benzylic Position: Halogenation

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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

Nucleophilic Aromatic Substitution: Elimination–Addition

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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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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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Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

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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...
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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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A continuous-flow protocol for light-induced benzylic fluorinations.

David Cantillo1, Oscar de Frutos, Juan A Rincón

  • 1Institute of Chemistry, University of Graz , Heinrichstrasse 28, A-8010 Graz, Austria.

The Journal of Organic Chemistry
|August 22, 2014
PubMed
Summary

This study introduces a continuous-flow method for light-induced fluorination of benzylic compounds using Selectfluor and xanthone. The efficient process achieves good to excellent yields in under 30 minutes.

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Area of Science:

  • Organic Chemistry
  • Photochemistry
  • Flow Chemistry

Background:

  • Fluorination of benzylic compounds is crucial for synthesizing pharmaceuticals and materials.
  • Developing efficient and sustainable fluorination methods remains an active area of research.
  • Continuous-flow chemistry offers advantages in safety, scalability, and reaction control.

Purpose of the Study:

  • To develop a novel continuous-flow protocol for the photo-induced fluorination of benzylic compounds.
  • To utilize an inexpensive and readily available photoorganocatalyst for this transformation.
  • To achieve high yields and selectivity under mild reaction conditions.

Main Methods:

  • A continuous-flow photoreactor was constructed using fluorinated ethylene propylene (FEP) tubing.
  • Selectfluor was employed as the fluorine source.
  • Xanthone was used as the photoorganocatalyst, activated by a compact fluorescent lamp (black-light).

Main Results:

  • The protocol demonstrated high efficiency for the fluorination of various benzylic substrates.
  • Good to excellent isolated yields were obtained for a diverse range of functionalized compounds.
  • Short residence times, below 30 minutes, were sufficient for high conversion.

Conclusions:

  • The developed continuous-flow protocol offers an efficient, rapid, and scalable method for benzylic fluorination.
  • The use of xanthone as a photoorganocatalyst under black-light irradiation is effective and cost-efficient.
  • This approach provides a valuable tool for accessing fluorinated organic molecules.