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Related Concept Videos

Preparation of Nitriles01:12

Preparation of Nitriles

2.8K
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...
2.8K
Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

9.6K
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.
9.6K
Nitriles to Ketones: Grignard Reaction00:57

Nitriles to Ketones: Grignard Reaction

7.5K
Organomagnesium halides, commonly known as Grignard reagents, convert nitriles to ketones and proceed through a nucleophilic acyl substitution. Nitriles react with a Grignard reagent, followed by an aqueous acid, to yield ketones. The reaction introduces a new carbon–carbon bond. The alkyl–magnesium bond in the Grignard reagent is highly polar, so the alkyl carbon develops a carbanionic character and acts as a nucleophile.
The mechanism begins with a nucleophilic attack by the Grignard...
7.5K
Crossed Aldol Reactions: Overview01:04

Crossed Aldol Reactions: Overview

6.5K
Crossed aldol addition is the reaction between two different carbonyl compounds under acidic or basic conditions. Here, both the carbonyl compounds function as nucleophiles and electrophiles. As shown in Figure 1, such a reaction yields a mixture of products, two of which are formed via self-condensation, while the remaining two are formed via crossed-condensation. Without adjustment, the reaction's usefulness in organic chemistry is decreased.
6.5K
Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

5.0K
Nitriles are reduced to amines in the presence of strong reducing agents like lithium aluminum hydride through a typical nucleophilic acyl substitution. The reaction requires two equivalents of the reducing agent. The reducing agent acts as a source of hydride ions.
As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to...
5.0K
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H

7.0K
All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for...
7.0K

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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

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Platinum-Electrocatalyzed Divergent Nitrile Cross-Coupling.

Wentao Xu1, Ping Hu1, Yifan Zhong1

  • 1The Institute for Advanced Studies (IAS), Wuhan University, Wuhan 430072, P. R. China.

JACS Au
|March 27, 2026
PubMed
Summary

Platinum chloride efficiently catalyzes nitrile cross-coupling reactions without complex ligands. This method uses platinum nanoparticles to synthesize diverse amines and carbamates, offering a modular platform for nitrile upgrading.

Keywords:
electroreductionelectrosynthesisnitrilesorganic electrochemistryreductive coupling

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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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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

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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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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Area of Science:

  • Catalysis
  • Organic Chemistry
  • Materials Science

Background:

  • Electrocatalytic hydrogenation has advanced using molecular complexes.
  • Active molecular catalysts often need complex ligands and conditions.

Purpose of the Study:

  • To demonstrate platinum chloride as an efficient catalyst precursor for nitrile cross-coupling reactions.
  • To develop a ligand-free, divergent strategy for nitrile functionalization.

Main Methods:

  • Utilized platinum chloride as a catalyst precursor without ligands.
  • Investigated nitrile cross-coupling with nucleophiles (amines) and electrophiles (chloroformates).
  • Performed mechanistic studies to identify active catalytic species.

Main Results:

  • Achieved efficient and selective synthesis of secondary and tertiary amines and organic carbamates.
  • Nitriles acted as ambiphilic reagents, coupling with diverse amines and chloroformates.
  • Mechanistic studies suggested platinum nanoparticles as the active species.

Conclusions:

  • Platinum chloride serves as an effective, ligand-free catalyst precursor for divergent nitrile cross-coupling.
  • The developed protocol offers a modular and divergent platform for electroreductive nitrile upgrading.
  • Platinum nanoparticles are likely the key catalytic species in this transformation.