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Related Concept Videos

Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

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Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...
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Electrophilic Aromatic Substitution: Nitration of Benzene01:20

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The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
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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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Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

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Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
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Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene01:11

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The Friedel–Crafts acylation reactions involve the addition of an acyl group to an aromatic ring. These reactions proceed via electrophilic aromatic substitution by employing an acyl chloride and a Lewis acid catalyst such as aluminum chloride to form aryl ketone.
9.6K
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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Related Experiment Video

Updated: Mar 15, 2026

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Nickel-Catalyzed Aromatic C-H Functionalization.

Junichiro Yamaguchi1, Kei Muto2, Kenichiro Itami3,4

  • 1Department of Applied Chemistry, Waseda University, Tokyo, 169-8555, Japan. junyamaguchi@waseda.jp.

Topics in Current Chemistry (Cham)
|August 31, 2016
PubMed
Summary

Nickel-catalyzed C-H functionalization offers an efficient route to complex molecules. This review highlights recent advances in nickel catalysis for aromatic C-H bond formation, including mechanisms and applications.

Keywords:
ArenesCatalystC–H activationC–H functionalizationHeteroarenesNickel

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Chemistry

Background:

  • Catalytic C-H functionalization enables efficient synthesis of complex molecules.
  • Transition metal catalysts are crucial for C-H activation.
  • Nickel catalysts offer a cost-effective alternative to precious metals.

Purpose of the Study:

  • To review recent advancements in nickel-catalyzed aromatic C-H functionalization.
  • To classify reactions by type and reaction partners.
  • To present reaction mechanisms and applications in natural product and pharmaceutical synthesis.

Main Methods:

  • Literature review of nickel-catalyzed C-H functionalization reactions.
  • Classification of reactions based on types and partners.
  • Discussion of reaction mechanisms and synthetic applications.

Main Results:

  • Nickel catalysis provides a versatile platform for C-H functionalization.
  • Recent progress includes diverse reaction types and partners.
  • Applications in synthesizing complex natural products and pharmaceuticals are demonstrated.

Conclusions:

  • Nickel-catalyzed aromatic C-H functionalization is a rapidly developing field.
  • It offers a powerful tool for constructing C-C and C-heteroatom bonds.
  • This methodology is increasingly applied in drug discovery and natural product synthesis.