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

Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)

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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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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

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

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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.
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Preparation of Nitriles01:12

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One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...
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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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Preparation of Alkynes: Alkylation Reaction02:27

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Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
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Nickel-Catalyzed Aryl Group Interconversion: A Non-Equilibrium Strategy for Aryl Nitrile Synthesis.

Hiroki Tanaka1, Eito Moriya1, Yuna Onozawa1

  • 1Department of Applied Chemistry, Waseda University, 513 Wasedatsurumakicho, Shinjuku, Tokyo 162-0041, Japan.

JACS Au
|February 27, 2026
PubMed
Summary

This study introduces a novel nickel-catalyzed reaction for aryl group interconversion, transforming aromatic esters into valuable nitriles. The process utilizes a unique decarbonylative step, avoiding excess reagents and enabling efficient synthesis.

Keywords:
aromatic estersaryl group interconversionaryl nitrilescyanationnickel

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Cross-electrophile coupling constructs C-C bonds using metal catalysis.
  • Aryl group interconversion swaps aromatic groups between electrophiles via ligand exchange.
  • Existing methods often require excess reagents due to reversibility.

Purpose of the Study:

  • To develop a nickel-catalyzed aryl group interconversion method.
  • To enable the transformation of aromatic esters into nitriles.
  • To establish an irreversible pathway for efficient synthesis.

Main Methods:

  • Nickel-catalyzed reaction between aromatic esters and 2-cyanopyridine.
  • Utilizing a decarbonylative ether formation step to drive the reaction.
  • Investigating the mechanism via oxidative addition and anionic ligand exchange.

Main Results:

  • Efficient synthesis of pharmaceutically relevant nitriles from aromatic esters.
  • Accommodates a wide range of aromatic ester substrates.
  • The reaction proceeds via irreversible decarbonylative ether formation and anionic CN/OPh ligand exchange.

Conclusions:

  • A novel, irreversible nickel-catalyzed aryl group interconversion is established.
  • This method overcomes limitations of traditional reversible aryl group exchange reactions.
  • The transformation provides a highly efficient route to valuable nitrile products.