Search research articles

ABOUT JoVE

Overview Leadership Blog JoVE Help Center

AUTHORS

Publishing Process Editorial Board Scope & Policies Peer Review FAQ Submit

LIBRARIANS

Testimonials Subscriptions Access Resources Library Advisory Board FAQ

RESEARCH

JoVE Journal Methods Collections JoVE Encyclopedia of Experiments Archive

EDUCATION

JoVE Core JoVE Business JoVE Science Education JoVE Lab Manual Faculty Resource Center Faculty Site

Terms & Conditions of Use

Related Concept Videos

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.

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.

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...

Amines to Alkenes: Hofmann Elimination

Amines to Alkenes: Hofmann Elimination

Alkenes can be obtained from amines via an E2 elimination. The amine is first converted into a good leaving group, such as a quaternary ammonium salt. This is accomplished by treating the amine with an excess of alkyl halide, which results in a halide salt. Next, the halide salt is transformed into a hydroxide salt that functions as a base to enable elimination.
Under thermal conditions, the hydroxide can abstract a proton from the β carbon; this generates an alkene with the simultaneous...

Amines to Amides: Acylation of Amines

Amines to Amides: Acylation of Amines

Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...

ortho–para-Directing Activators: –CH3, –OH, –&NoBreak;NH2, –OCH3

ortho–para-Directing Activators: –CH₃, –OH, –⁠NH₂, –OCH₃

All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by

Same author

Molecular Mechanisms of Cellulase Biosynthesis in Trichoderma reesei: Regulatory Networks, Secretion Pathways, and Environmental Modulation.

Biotechnology journal·2026

Same author

Adverse childhood experiences and household firearm ownership: A large-scale analysis of specific risk factors among 15,771 adults from four U.S. states.

Preventive medicine·2026

Same author

Sulfur Vacancy-Engineered 2D/2D ZnIn<sub>2</sub>S<sub>4</sub>/Zn-TCPP S-Scheme Heterojunction for Efficient Photocatalytic H<sub>2</sub>O<sub>2</sub> Production.

Small (Weinheim an der Bergstrasse, Germany)·2026

Same author

Cross-model diffusion: Mitigating hallucination in large language models for rumor detection.

Neural networks : the official journal of the International Neural Network Society·2026

Same author

Global trends in robotic-assisted laparoscopic surgery (RALS): a bibliometric analysis (2000-2024).

Updates in surgery·2026

Same author

Stereodivergent Synthesis of Allylic Phosphonates.

The Journal of organic chemistry·2026

Search research articles

Related Experiment Video

Updated: Sep 11, 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

Continuous Flow Electrochemistry Unlocks Broadly Applicable Arene C─H Amination.

Tian-Sheng Chen¹, Peng Xiong¹, Hai-Chao Xu¹

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

Angewandte Chemie (International Ed. in English)

|August 18, 2025

Summary

This summary is machine-generated.

This study presents a new continuous flow electrochemical C─H amination method for synthesizing arylamines. The process efficiently functionalizes diverse arenes, overcoming limitations of existing C─H amination techniques.

Keywords:

Amination Aniline C‐H functionalization Flow Electrochemistry Synthetic methods

More Related Videos

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

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

Published on: January 4, 2018

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

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

Published on: June 21, 2017

Related Experiment Videos

Last Updated: Sep 11, 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

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

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

Published on: January 4, 2018

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

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
Electrochemistry
Sustainable Synthesis

Background:

Direct C─H amination is key for arylamine synthesis.
Current methods face challenges with substrate scope, selectivity, and scalability, especially for electron-deficient arenes.

Purpose of the Study:

To develop a continuous flow electrochemical C─H amination method.
To enable efficient functionalization of arenes with diverse electronic properties.
To address limitations of existing C─H amination strategies.

Main Methods:

A pyridination-aminolysis sequence was employed.
Continuous flow electrochemical conditions were utilized, avoiding divided cells, strong oxidants, or transition-metal catalysts.
The method was scaled up using parallel microreactors over 4 days.

Main Results:

Efficient functionalization of electron-rich, electron-deficient, and halogenated arenes, as well as heterocycles.
Excellent functional group tolerance was demonstrated.
Over 100 grams of aniline product were produced with high efficiency during scaled-up continuous operation.

Conclusions:

Continuous flow electrochemistry offers a versatile and practical platform for sustainable C─H functionalization.
The developed method expands the scope and efficiency of arene amination.
This approach provides a scalable and environmentally conscious alternative for synthesizing arylamines.