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Limitations of Friedel–Crafts Reactions01:26

Limitations of Friedel–Crafts Reactions

5.5K
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

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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...
6.7K
Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene01:11

Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene

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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.
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Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation01:22

Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation

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Baeyer–Villiger oxidation converts aldehydes to carboxylic acids and ketones to esters. The reaction uses peroxy acids or peracids and is often catalyzed by acid. The reaction is named after its pioneers, Adolf von Baeyer and Victor Villiger. The reaction is achieved by a wide range of peracids such as m-chloroperoxybenzoic acid (mCPBA), perbenzoic acid (C6H5COOOH), peracetic acid (CH3COOOH), hydrogen peroxide (H2O2), and tert-butyl hydroperoxide (t-BuOOH).
The carbonyl center is...
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Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.7K
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.
2.7K
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism01:13

Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism

8.1K
Carboxylic acids react with alcohols to yield esters via an acid-catalyzed condensation reaction called Fischer esterification. This is a nucleophilic acyl substitution reaction that proceeds via a tetrahedral intermediate, where a water molecule is eliminated as the leaving group.
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Biocatalytic Friedel-Crafts Reactions.

Reuben B Leveson-Gower1, Gerard Roelfes1

  • 1Stratingh Institute for Chemistry University of Groningen 9747 AG Groningen The Netherlands.

Chemcatchem
|January 6, 2023
PubMed
Summary

Enzymes and bio-hybrid catalysts offer greener alternatives to traditional chemical methods for Friedel-Crafts reactions. These biocatalysts enable efficient synthesis of important molecular linkages under mild conditions.

Keywords:
AcylationArtificial EnzymesBiocatalysisDNA CatalysisEnzymesFriedel-Crafts Alkylation

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Area of Science:

  • Synthetic Chemistry
  • Biocatalysis
  • Green Chemistry

Background:

  • Friedel-Crafts alkylation and acylation are crucial for synthesizing molecules with aryl-alkyl and aryl-acyl linkages found in bioactive compounds.
  • Nature utilizes these reactions in biosynthetic pathways.
  • Current chemical methods can be inefficient and toxic.

Purpose of the Study:

  • To review advancements in enzymatic and bio-hybrid Friedel-Crafts catalysts.
  • To explore mechanistic aspects and synthetic utility.
  • To identify future directions for more efficient and sustainable Friedel-Crafts reactions.

Main Methods:

  • Directed evolution of enzymes for unnatural substrates.
  • Development of bio-hybrid catalysts by anchoring chemical catalysts into biomolecular scaffolds.
  • Review of mechanistic studies and synthetic applications.

Main Results:

  • Engineered enzymes demonstrate expanded substrate scope for Friedel-Crafts reactions.
  • Bio-hybrid catalysts combine benefits of chemical catalysis and biomolecular scaffolds.
  • Both approaches offer milder reaction conditions compared to traditional methods.

Conclusions:

  • Enzymatic and bio-hybrid catalysts represent promising, sustainable alternatives to conventional Friedel-Crafts chemistry.
  • Further research can lead to highly efficient and environmentally benign synthetic methodologies.
  • These advancements are key to the future of green chemistry in industrial applications.