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Limitations of Friedel–Crafts Reactions01:26

Limitations of Friedel–Crafts Reactions

5.1K
Several restrictions limit the use of Friedel–Crafts reactions. First, the halogen in the alkyl halide must be attached to an sp3-hybridized carbon for the Friedel–Crafts reactions to occur. Vinyl or aryl halides do not react since the carbocations formed are unstable under the reaction conditions. Second, Friedel–Crafts alkylation is susceptible to carbocation rearrangement, and the major products obtained have a rearranged carbon skeleton. In contrast, the acylium ion is...
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Electrophilic Aromatic Substitution: Friedel–Crafts Alkylation of Benzene01:17

Electrophilic Aromatic Substitution: Friedel–Crafts Alkylation of Benzene

6.2K
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...
6.2K
Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene01:11

Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene

6.6K
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.
6.6K
Olefin Metathesis Polymerization: Overview01:13

Olefin Metathesis Polymerization: Overview

2.0K
Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
Ruthenium-based Grubbs catalyst is the most commonly used catalyst for olefin metathesis polymerization. Grubbs catalyst consists...
2.0K
Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

4.6K
Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
4.6K
Electrophilic Aromatic Substitution: Sulfonation of Benzene01:22

Electrophilic Aromatic Substitution: Sulfonation of Benzene

5.4K
Sulfonation of benzene is a reaction wherein benzene is treated with fuming sulfuric acid at room temperature to produce benzenesulfonic acid. Fuming sulfuric acid is a mixture of sulfur trioxide and concentrated sulfuric acid.
5.4K

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Updated: May 7, 2025

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
08:56

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

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Sulfonated polystyrene foam waste as an efficient catalyst for Friedel-Crafts type reactions.

Behrang Moazzen1, Roya Kamrouz1, Alireza Khorshidi2

  • 1Faculty of Chemistry, University of Guilan, P. O. Box: 41335-1914, Rasht, Iran.

Scientific Reports
|January 3, 2025
PubMed
Summary

Sulfonated polystyrene foam waste (SPS) shows high catalytic efficiency in Friedel-Crafts reactions, outperforming sulfonated gamma alumina. This sustainable catalyst is effective for synthesizing valuable organic compounds from plastic waste.

Keywords:
Friedel-crafts type reactionFunctionalizationIndoleOxiranePolystyrene foam waste

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Area of Science:

  • Catalysis
  • Materials Science
  • Organic Synthesis

Background:

  • Friedel-Crafts reactions are crucial in organic synthesis.
  • Developing efficient and sustainable catalysts is an ongoing challenge.
  • Valorization of plastic waste offers environmental and economic benefits.

Purpose of the Study:

  • To compare the catalytic efficiency of sulfonated polystyrene foam waste (SPS) and sulfonated gamma alumina (SGA).
  • To evaluate SPS as a sustainable catalyst for Friedel-Crafts type reactions.
  • To explore the synthesis of bis(indolyl)methanes using SPS.

Main Methods:

  • Characterization of SPS and SGA using state-of-the-art techniques.
  • Catalytic testing in the regioselective ring-opening of 2-(phenoxymethyl)oxirane with indole.
  • Assessment of catalyst recyclability and stability.
  • Synthesis of bis(indolyl)methanes under solvent-free conditions.

Main Results:

  • SPS exhibited a higher load of -SO3H functional groups (1.62 mmol H+/g) than SGA (1.23 mmol H+/g).
  • SPS demonstrated efficient catalysis for the reaction of indoles and oxiranes, yielding 55-99%.
  • SPS effectively synthesized various bis(indolyl)methanes with yields ranging from 88-99%.
  • SPS maintained significant catalytic activity over multiple reuse cycles.

Conclusions:

  • SPS is a highly efficient and recyclable catalyst for Friedel-Crafts type reactions.
  • SPS offers a sustainable and greener alternative to conventional catalysts.
  • This study promotes the valorization of plastic waste in organic synthesis.