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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...
Limitations of Friedel–Crafts Reactions01:26

Limitations of Friedel–Crafts Reactions

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 stabilized by...
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.
Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

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.
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
Acid-Catalyzed Aldol Addition Reaction01:15

Acid-Catalyzed Aldol Addition Reaction

The aldol reaction of a ketone under acidic conditions successfully forms an unsaturated carbonyl as the final product instead of an aldol. The acid-catalyzed aldol reaction is depicted in Figure 1.

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Related Experiment Video

Updated: Jul 7, 2026

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
09:58

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts

Published on: February 24, 2015

Exploring a chemical encoding strategy for combinatorial synthesis using Friedel-Crafts alkylation.

Robin H Scott1, Colin Barnes, Ulrich Gerhard

  • 1University Chemical Laboratory, University of Cambridge, Lensfield Road, Cambridge, UK CB2 1EW.

Chemical Communications (Cambridge, England)
|February 9, 2008
PubMed
Summary

Scandium(III) and ytterbium(III) triflate catalysts enable mild Friedel-Crafts alkylation for attaching hydroxymethyl pyrrole amide tags to resins. This facilitates the creation of split and mix peptide libraries.

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Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Last Updated: Jul 7, 2026

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
09:58

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts

Published on: February 24, 2015

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

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Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Polymer Science

Background:

  • Friedel-Crafts alkylation is a fundamental reaction in organic synthesis.
  • Developing efficient catalytic systems for functionalizing polymer resins is crucial for combinatorial chemistry.
  • Lanthanide triflates are increasingly recognized for their catalytic activity in various organic transformations.

Purpose of the Study:

  • To demonstrate the utility of scandium(III) triflate and ytterbium(III) triflate as catalysts for Friedel-Crafts alkylation.
  • To functionalize polystyrene resins with hydroxymethyl pyrrole amide tags under mild conditions.
  • To enable the encoding of split and mix peptide libraries using this methodology.

Main Methods:

  • Utilized scandium(III) triflate and ytterbium(III) triflate as Lewis acid catalysts.
  • Performed Friedel-Crafts alkylation reactions to attach hydroxymethyl pyrrole amide tags (compounds 1b-i) to polystyrene resins.
  • Employed mild reaction conditions to preserve the integrity of the resin and tags.

Main Results:

  • Successfully demonstrated the catalytic activity of scandium(III) triflate and ytterbium(III) triflate in the alkylation of polystyrene resins.
  • Achieved efficient insertion of hydroxymethyl pyrrole amide tags onto the resins.
  • Established a method for encoding split and mix peptide libraries.

Conclusions:

  • Scandium(III) triflate and ytterbium(III) triflate are effective catalysts for mild Friedel-Crafts alkylation on polystyrene resins.
  • This method provides a viable route for the synthesis of functionalized resins and peptide library construction.