Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Amines to Alkenes: Hofmann Elimination01:16

Amines to Alkenes: Hofmann Elimination

2.7K
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...
2.7K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism01:26

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

3.7K
The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl azides. In the Hofmann rearrangement, a primary amide undergoes deprotonation in the presence of a base, followed by halogenation to generate an N-haloamide. A second proton abstraction produces a stabilized anionic species, which rearranges to an isocyanate intermediate via an alkyl group migration from the carbonyl carbon to the neighboring...
3.7K
Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

3.3K
Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
3.3K
Amines to Alkenes: Cope Elimination01:14

Amines to Alkenes: Cope Elimination

2.1K
Cope elimination reaction involves the conversion of tertiary amines to alkene using hydrogen peroxide under thermal conditions, as depicted in figure 1.
2.1K
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

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

6.6K
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...
6.6K
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

2.8K
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...
2.8K

You might also read

Related Articles

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

Sort by
Same author

Ligand-Controlled Chemoselective and Enantioselective Cyclization of Enynes With Aroyl Chlorides.

Angewandte Chemie (International ed. in English)·2026
Same author

Synthesis of Polysubstituted Pyrroles via (2 + 2 + 1) Cyclization of Enone Oxime Ethers with Alkynes and Diaziridinone.

The Journal of organic chemistry·2026
Same author

Ligand-Controlled Acyl and Decarbonylative Sonogashira Cross-Coupling of α,β-Unsaturated Thioesters.

Organic letters·2025
Same author

Ring expansion of 3-hydroxyoxindoles to 4-quinolones <i>via</i> palladium-catalyzed C-C(acyl) bond cleavage.

Chemical communications (Cambridge, England)·2024
Same author

Palladium-Catalyzed Directed Carbon-Carbon Bond Activation of Aryl Nitriles for Cyano Transfer.

Organic letters·2024
Same author

Palladium-Catalyzed Deuteration of Arylketone Oxime Ethers.

Angewandte Chemie (International ed. in English)·2024

Related Experiment Video

Updated: Oct 15, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
08:43

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

10.4K

Copper-Mediated ortho-C-H Amination Using DMF as the Amine Source.

Tai-Jin Cheng1,2, Jun-Jie Chen1, Peng Wu3

  • 1Chinese Academy of Sciences Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, University of Chinese Academy of Sciences, Shanghai 201203, China.

Organic Letters
|October 27, 2021
PubMed
Summary

This study introduces a novel copper-catalyzed ortho-C-H amination of anilines. The method efficiently uses oxalamide directing groups and dimethylformamide (DMF) for amination, proving practical for drug modification.

More Related Videos

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
07:50

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Published on: May 26, 2019

9.4K
[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
09:12

[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

Published on: May 21, 2019

9.5K

Related Experiment Videos

Last Updated: Oct 15, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
08:43

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

10.4K
Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
07:50

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Published on: May 26, 2019

9.4K
[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
09:12

[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

Published on: May 21, 2019

9.5K

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Direct C-H functionalization offers efficient synthetic routes.
  • Ortho-amination of anilines remains a synthetic challenge.
  • Developing new catalytic systems for C-H activation is crucial.

Purpose of the Study:

  • To develop a novel copper-catalyzed ortho-C-H amination of anilines.
  • To utilize oxalamide as a directing group for regioselective amination.
  • To demonstrate the utility of the protocol in late-stage drug functionalization.

Main Methods:

  • Copper-mediated C-H amination reaction.
  • Utilizing oxalamide as a directing group.
  • Employing dimethylformamide (DMF) as the amination reagent.

Main Results:

  • Successful ortho-C-H amination of anilines achieved.
  • The protocol exhibits tolerance to diverse functional groups.
  • Good compatibility with various heterocyclic systems was observed.
  • Demonstrated synthetic practicality through late-stage drug dimethylamination.

Conclusions:

  • A novel and practical copper-catalyzed ortho-C-H amination protocol has been established.
  • The developed method offers broad functional group tolerance and heterocyclic compatibility.
  • Mechanistic studies suggest a potential radical pathway, offering insights for further development.