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Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene

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.

Electrophilic Aromatic Substitution: Friedel–Crafts Alkylation of Benzene

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...

Electrophilic Aromatic Substitution: Overview

Electrophilic Aromatic Substitution: Overview

In an electrophilic aromatic substitution reaction, an electrophile substitutes for a hydrogen of an aromatic compound.

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.

Thermal Electrocyclic Reactions: Stereochemistry

Thermal Electrocyclic Reactions: Stereochemistry

The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...

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Updated: Sep 5, 2025

Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid

Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid

Published on: November 15, 2017

Electrochemical aromatic C-H hydroxylation in continuous flow.

Hao Long^1,2, Tian-Sheng Chen¹, Jinshuai Song³

¹State Key Laboratory of Physical Chemistry of Solid Surfaces, College of Chemistry and Chemical Engineering, Xiamen University, 361005, Xiamen, China.

Nature Communications

|July 8, 2022

Summary

This study introduces an electrochemical method for arene C-H hydroxylation, enabling efficient and scalable synthesis of phenols under mild conditions without chemical oxidants.

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Last Updated: Sep 5, 2025

Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid

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Published on: November 15, 2017

Utilization of Stop-flow Micro-tubing Reactors for the Development of Organic Transformations

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A Scalable Balz-Schiemann Reaction Protocol in a Continuous Flow Reactor

A Scalable Balz-Schiemann Reaction Protocol in a Continuous Flow Reactor

Published on: February 10, 2023

Area of Science:

Organic Chemistry
Electrochemistry
Sustainable Synthesis

Background:

Direct arene C-H bond hydroxylation is challenging due to regioselectivity and overoxidation issues.
Existing methods often require harsh conditions, catalysts, or chemical oxidants.

Purpose of the Study:

To develop a novel electrochemical method for direct arene C-H hydroxylation.
To achieve efficient and regioselective synthesis of phenols.
To demonstrate scalability and mild reaction conditions.

Main Methods:

Electrochemical oxidation of arenes in a continuous flow system.
Utilized mild conditions, avoiding catalysts and chemical oxidants.
Investigated compatibility with arenes of diverse electronic properties.

Main Results:

Achieved direct C-H hydroxylation of arenes to produce phenols.
Demonstrated broad substrate scope, accommodating various electronic properties.
Showcased excellent scalability with continuous production of 1 mol (204 grams) of a phenol product.

Conclusions:

The developed electrochemical flow method offers a sustainable and efficient route to phenols.
This approach overcomes limitations of traditional C-H hydroxylation methods.
The process is scalable and operates under mild, catalyst-free conditions.