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Related Concept Videos

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

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.
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

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...
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para position.
ortho–para-Directing Deactivators: Halogens01:24

ortho–para-Directing Deactivators: Halogens

Halogens are ortho–para directors. They are more electronegative than carbon. Therefore, as ring substituents, they can withdraw electrons through the inductive effect and deactivate the aromatic ring towards electrophilic substitution. Halogens also have an electron-donating resonance effect on the ring, which influences the orientation of the incoming electrophile. If an electrophile attacks at the ortho or the para position, the halogen donates electrons and stabilizes the intermediate...
Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.

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Related Experiment Video

Updated: Jul 12, 2026

Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
10:10

Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes

Published on: July 28, 2018

Mild C─F Activation of Azido(per)Fluoroalkanes.

Olena Shaitanova1,2, María Martínez Mallo1,3, Sergii Suikov1

  • 1Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Prague, Czechia.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|July 10, 2026
PubMed
Summary

Researchers developed a new method for activating C(sp3)-F bonds in fluorinated azidoalkanes using electrophilic azides. This approach enables mild, high-yield synthesis of diverse sulfur-containing compounds without metal catalysts.

Keywords:
1,2,3‐triazoleC─F activationPFASazide

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Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
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Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

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Preparation of Hydrophobic Metal-Organic Frameworks via Plasma Enhanced Chemical Vapor Deposition of Perfluoroalkanes for the Removal of Ammonia
12:05

Preparation of Hydrophobic Metal-Organic Frameworks via Plasma Enhanced Chemical Vapor Deposition of Perfluoroalkanes for the Removal of Ammonia

Published on: October 10, 2013

Related Experiment Videos

Last Updated: Jul 12, 2026

Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
10:10

Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes

Published on: July 28, 2018

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
04:38

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

Published on: July 28, 2022

Preparation of Hydrophobic Metal-Organic Frameworks via Plasma Enhanced Chemical Vapor Deposition of Perfluoroalkanes for the Removal of Ammonia
12:05

Preparation of Hydrophobic Metal-Organic Frameworks via Plasma Enhanced Chemical Vapor Deposition of Perfluoroalkanes for the Removal of Ammonia

Published on: October 10, 2013

Area of Science:

  • Organic Chemistry
  • Fluorine Chemistry
  • Catalysis

Background:

  • Carbon-fluorine (C-F) bonds are prevalent in pharmaceuticals and materials but challenging to activate selectively.
  • Existing C-F activation methods often require harsh conditions, expensive catalysts, or lack functional group tolerance.

Purpose of the Study:

  • To develop a novel, mild, and selective method for activating C(sp3)-F bonds in fluorinated azidoalkanes.
  • To synthesize new nitrogen- and sulfur-containing organic scaffolds from readily available fluorinated azides.

Main Methods:

  • Utilizing electrophilic azide groups to promote fluoride elimination and subsequent nucleophilic addition.
  • Employing mild reaction conditions with inexpensive reagents, avoiding metal catalysts and external energy input.
  • Conducting mechanistic investigations using spectroscopy, X-ray crystallography, and ab initio calculations.

Main Results:

  • Achieved rapid, high-yield transformations of (per)fluoroalkyl azides into diverse sulfur-containing azides, imines, and triazoles.
  • Demonstrated broad functional group tolerance, including compatibility with thiol-sensitive motifs.
  • Elucidated the reaction mechanism involving key azide intermediates and a denitrogenation pathway.

Conclusions:

  • The developed method offers a practical and scalable route for C-F bond activation in fluorinated azidoalkanes.
  • This approach provides access to valuable nitrogen- and sulfur-functionalized compounds under mild conditions.
  • Advances the field of C-F activation chemistry with a versatile and efficient transformation.