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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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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...
5.0K
Structure of Benzene: Molecular Orbital Model01:18

Structure of Benzene: Molecular Orbital Model

11.8K
According to the molecular orbital (MO) model, benzene has a planar structure with a regular hexagon of six sp2 hybridized carbons. As shown in Figure 1, each carbon is bonded to three other atoms with C–C–C and H–C–C bond angles of 120°. The C–H bond length is 109 pm, and the C–C bond length is 139 pm which is midway between the single bond length of sp3 hybridized carbons (154 pm) and sp2 hybridized carbons (133 pm).
11.8K
NMR Spectroscopy of Benzene Derivatives01:34

NMR Spectroscopy of Benzene Derivatives

10.8K
Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling...
10.8K
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

10.5K
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...
10.5K
Structure of Benzene: Kekulé Model01:07

Structure of Benzene: Kekulé Model

11.5K
In 1865, August Kekule suggested the structure of benzene according to the structural theory of organic chemistry based on the three assertions—formula of benzene is C6H6, all the hydrogens of benzene are equivalent, and each carbon must have four bonds due to its tetravalency.
He proposed that benzene has a cyclic structure of six carbon atoms attached to one hydrogen atom each, with three alternating pi bonds.
11.5K

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Updated: Jan 6, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

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Fluorocarbyne Insertion into Benzene Skeletons.

Cheng-Jie Wu1, Ming-Yang Wang1, Cheng Wang1

  • 1Department of Chemistry, Zhejiang University, Hangzhou 310058, China.

Journal of the American Chemical Society
|November 25, 2025
PubMed
Summary

Researchers developed a novel fluorocarbyne reaction to convert simple benzene into valuable monofluorinated cycloheptatrienes. This method offers broad functional group tolerance and selective meta-insertion, advancing organofluorine chemistry and drug discovery.

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Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
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Qualitative Identification of Carboxylic Acids, Boronic Acids, and Amines Using Cruciform Fluorophores
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Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
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Qualitative Identification of Carboxylic Acids, Boronic Acids, and Amines Using Cruciform Fluorophores
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Area of Science:

  • Organofluorine Chemistry
  • Synthetic Organic Chemistry

Background:

  • Fluorinated synthons are crucial in organofluorine chemistry.
  • Metal-fluorocarbyne synthons are underexplored compared to trifluoromethyl and difluorocarbene counterparts.

Purpose of the Study:

  • To report the first application of metal-fluorocarbyne in organic synthesis.
  • To enable concurrent fluorine incorporation and skeletal editing of arenes.

Main Methods:

  • Fluorocarbyne-promoted skeletal editing reaction.
  • Benzene transformation into monofluorinated cycloheptatrienes.
  • Mechanistic studies including intermediate capture and DFT calculations.

Main Results:

  • Achieved selective benzene activation and meta-insertion into cycloheptatrienes.
  • Demonstrated broad functional group tolerance and compatibility with diverse arene substrates.
  • Successfully applied to late-stage drug modification, enhancing solubility of tecovirimat.

Conclusions:

  • This work introduces metal-fluorocarbyne as a versatile tool for fluorine incorporation and scaffold modification.
  • The developed method offers a new pathway for synthesizing fluorinated compounds with potential pharmaceutical applications.