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Related Concept Videos

Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

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 confirmed through isotopic...
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary amide...
Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)

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 the...
Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

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...
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.

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Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
09:35

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

Catalytic C-H amination with aromatic amines.

Raymond T Gephart1, Daria L Huang, Mae Joanne B Aguila

  • 1Department of Chemistry, Georgetown University, Box 571227, Washington, DC 20057-1227, USA.

Angewandte Chemie (International Ed. in English)
|May 17, 2012
PubMed
Summary
This summary is machine-generated.

A new copper(I) catalyst facilitates C-H amination of anilines, even electron-poor ones, using low loadings. This method prevents unwanted diazene formation, broadening the scope of C-H functionalization reactions.

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

Published on: July 30, 2017

Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Organic Synthesis

Background:

  • C-H amination is a crucial transformation in organic synthesis.
  • Copper-catalyzed reactions offer sustainable alternatives.
  • Aniline derivatives are important building blocks but challenging substrates.

Purpose of the Study:

  • To develop a novel catalytic system for C-H amination of anilines.
  • To achieve high efficiency using low catalyst loadings.
  • To prevent the formation of undesired diazene byproducts.

Main Methods:

  • Utilized a β-diketiminato copper(I) complex as the catalyst.
  • Investigated the C-H amination of various aniline derivatives, including electron-poor and N-alkyl anilines.
  • Optimized reaction conditions to minimize diazene formation.

Main Results:

  • The copper(I) catalyst successfully enabled C-H amination of anilines.
  • Low catalyst loadings were effective, preventing oxidation to diazene (ArN=NAr).
  • Electron-poor and N-alkyl anilines were shown to be competent substrates.

Conclusions:

  • A novel and efficient copper-catalyzed C-H amination of anilines has been established.
  • The developed method offers a selective route to functionalized anilines, avoiding diazene formation.
  • This work expands the utility of copper catalysis in C-H functionalization.