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Related Concept Videos

Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

1.9K
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
1.9K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

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

2.0K
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
Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

9.4K
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.
9.4K
Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

2.7K
Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
2.7K
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

2.1K
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,...
2.1K
Preparation of Alkynes: Dehydrohalogenation02:34

Preparation of Alkynes: Dehydrohalogenation

17.1K
Introduction
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
17.1K

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Updated: Apr 30, 2026

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

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Palladium-catalyzed C(sp²)-H arylation using formamide as a transformable directing group.

Congqing Wan1, Jiaji Zhao, Mingfang Xu

  • 1Department of Bioengineering, College of Life Science and Technology, Jinan University , Guangzhou 510632, China.

The Journal of Organic Chemistry
|April 26, 2014
PubMed
Summary
This summary is machine-generated.

A novel palladium-catalyzed C-H activation process enables ortho arylation of formanilides. Formamide acts as a directing group, yielding biarylformanilides that can be converted into biarylisocyanides or N-heterocycles.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Palladium-catalyzed C-H activation is a powerful tool in organic synthesis.
  • Directing groups are crucial for regioselective functionalization.
  • Formamide derivatives have been explored for various chemical transformations.

Purpose of the Study:

  • To develop a new method for the ortho arylation of formanilides.
  • To investigate the utility of formamide as a transformable directing group in C-H functionalization.
  • To demonstrate the synthetic versatility of the resulting biarylformanilide products.

Main Methods:

  • Palladium-catalyzed cross-coupling reaction.
  • C-H activation strategy.
  • Use of formanilide substrates and arylating agents.

Main Results:

  • Successful ortho arylation of formanilides was achieved.
  • Formamide was validated as an effective directing group for this transformation.
  • The synthesized biarylformanilides were efficiently converted to biarylisocyanides and N-heterocycles.

Conclusions:

  • A novel and efficient palladium-catalyzed ortho arylation of formanilides has been established.
  • The formamide group serves as a versatile and transformable directing group.
  • This methodology provides access to valuable biaryl compounds and heterocyclic scaffolds.