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Related Concept Videos

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

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Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
2.0K
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

2.2K
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,...
2.2K
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

4.1K
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...
4.1K
Preparation of Nitriles01:12

Preparation of Nitriles

2.2K
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...
2.2K
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)

4.0K
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...
4.0K
Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

6.4K
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.
6.4K

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Updated: Sep 9, 2025

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
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Nickel-Catalyzed Cyanation of Aryl Halides.

Zhenqiang Ma1, Cuimeng Huo1, Duo Zhou1

  • 1Henan Province Key Laboratory of Environmentally Friendly Functional Materials, Institute of Chemistry, Henan Academy of Sciences, Zhengzhou 450002, China.

Molecules (Basel, Switzerland)
|August 28, 2025
PubMed
Summary

Nickel catalysis offers a sustainable and mild route for synthesizing aryl nitriles from aryl halides. This review covers recent advances using various cyanide sources and highlights future directions in this important chemical transformation.

Keywords:
aryl halidescyanationnickel catalysis

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Green Chemistry

Background:

  • Aryl nitriles are crucial building blocks in pharmaceuticals, agrochemicals, and materials science.
  • Traditional cyanation methods often require harsh conditions and toxic reagents.
  • Nickel catalysis presents a milder, more efficient, and versatile alternative.

Purpose of the Study:

  • To systematically review recent advancements in nickel-catalyzed cyanation of aryl halides.
  • To categorize developments based on diverse cyanide sources.
  • To highlight key aspects of catalyst design, mechanism, and sustainability.

Main Methods:

  • Review of literature on nickel-catalyzed cyanation reactions.
  • Categorization of cyanide sources into metal and non-metal/organic types.
  • Analysis of catalyst systems, ligand effects, and mechanistic studies.

Main Results:

  • Successful nickel-catalyzed cyanation achieved using various metal cyanides (e.g., NaCN, KCN, Zn(CN)2, K4[Fe(CN)6]).
  • Demonstrated utility of non-metal/organic cyanide sources (e.g., MeCN, nitriles, BrCN, CO2/NH3).
  • Significant progress in catalyst development, ligand design, and understanding reaction mechanisms.

Conclusions:

  • Nickel-catalyzed cyanation is a powerful and sustainable method for aryl nitrile synthesis.
  • The field has advanced significantly with diverse cyanide sources and improved catalytic systems.
  • Further research is needed to address remaining challenges and explore new green chemistry applications.