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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...
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

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, or cyano...
Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene01:11

Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene

The Friedel–Crafts acylation reactions involve the addition of an acyl group to an aromatic ring. These reactions proceed via electrophilic aromatic substitution by employing an acyl chloride and a Lewis acid catalyst such as aluminum chloride to form aryl ketone.
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...
Electrophilic Aromatic Substitution: Friedel–Crafts Alkylation of Benzene01:17

Electrophilic Aromatic Substitution: Friedel–Crafts Alkylation of Benzene

Friedel–Crafts reactions were developed in 1877 by the French chemist Charles Friedel and the American chemist James Crafts. Friedel–Crafts alkylation refers to the replacement of an aromatic proton with an alkyl group via electrophilic aromatic substitution. A Lewis acid catalyst such as aluminum chloride reacts with an alkyl halide to form a carbocation. The resulting carbocation then reacts with the aromatic ring and undergoes a series of electron rearrangements before giving the final...
Ketones with Nonenolizable Aromatic Aldehydes: Claisen–Schmidt Condensation01:01

Ketones with Nonenolizable Aromatic Aldehydes: Claisen–Schmidt Condensation

Benzaldehyde, like formaldehyde, lacks an α hydrogen and cannot enolize to form an enolate. Hence, the reaction of benzaldehyde with a ketone in the presence of an aqueous base forms a single crossed product. This reaction is referred to as Claisen–Schmidt condensation.
As the self-condensation of ketones is generally not favored in basic conditions, the self-condensed products do not form in the reaction between ketones and benzaldehyde. The general reaction of Claisen–Schmidt condensation is...

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Updated: Jun 18, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

Published on: April 1, 2013

An aromatic Glaser-Hay reaction.

Hien-Quang Do1, Olafs Daugulis

  • 1Department of Chemistry, University of Houston, Houston, Texas 77204-5003, USA.

Journal of the American Chemical Society
|November 11, 2009
PubMed
Summary

A new copper-catalyzed method enables the deprotonative dimerization of arenes using oxygen as an oxidant. This versatile reaction works for various electron-rich and electron-poor aromatic compounds, tolerating diverse functional groups.

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Arene functionalization is crucial in organic synthesis.
  • Developing efficient and selective methods for C-H bond activation and coupling is a key challenge.
  • Copper catalysis offers a sustainable and cost-effective approach for organic transformations.

Purpose of the Study:

  • To develop a general and efficient method for the copper-catalyzed deprotonative dimerization of arenes.
  • To utilize oxygen as a green terminal oxidant for arene coupling reactions.
  • To explore the substrate scope and functional group tolerance of the developed method.

Main Methods:

  • Copper-catalyzed reaction.
  • Deprotonative dimerization of arenes.

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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
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  • Utilizing molecular oxygen as the terminal oxidant.
  • Screening of catalysts, ligands, and reaction conditions.

    • Main Results:

    • A general method for copper-catalyzed deprotonative dimerization of arenes was established.
    • The reaction effectively couples electron-rich and electron-poor heterocycles, as well as electron-poor arenes.
    • The developed methodology demonstrates tolerance towards various functional groups, including nitro, cyano, dialkylamino, and ester groups.
    • Oxygen was successfully employed as the terminal oxidant, highlighting the green aspect of the reaction.

    Conclusions:

    • A novel and versatile copper-catalyzed deprotonative dimerization of arenes has been successfully developed.
    • The method offers a sustainable approach using oxygen as the oxidant and exhibits broad substrate scope and functional group tolerance.
    • This work provides a valuable tool for the synthesis of complex aromatic compounds through C-H activation and dimerization.