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

Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

2.1K
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.
2.1K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

1.8K
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
1.8K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

10.0K
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
10.0K
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

4.6K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
4.6K
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.5K
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.
2.5K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

3.7K
Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
3.7K

You might also read

Related Articles

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

Sort by
Same author

Site-Selective Peptide and Protein Functionalization with Cyclopropenium Cations.

Angewandte Chemie (International ed. in English)·2025
Same author

Catalytic Oxidative Ligand Transfer of Rh-Carbynoids and Alkyl Iodides.

Journal of the American Chemical Society·2025
Same author

Rh-Catalyzed Atroposelective Single-Carbon Insertion.

Journal of the American Chemical Society·2025
Same author

Rh-catalysed single-carbon insertion to 1,3-dienes.

Chemical science·2025
Same author

Rh-Catalyzed Enantioselective Aryl C-H Bond Cyclopropylation.

Journal of the American Chemical Society·2025
Same author

Late-Stage Photoredox-Catalyzed Aryl C-H Bond Diazomethylation with Atomic Carbon Reagents.

Journal of the American Chemical Society·2025

Related Experiment Video

Updated: Jun 5, 2025

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
12:27

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes

Published on: September 8, 2013

10.8K

Single-Carbon Insertion into Single C-C Bonds with Diazirines.

Valero G Alfonso1,2, Karen de la Vega-Hernández1, Marcos G Suero1,3

  • 1Institute of Chemical Research of Catalonia (ICIQ-CERCA), The Barcelona Institute of Science and Technology, Països Catalans 16, 43007 Tarragona, Spain.

Journal of the American Chemical Society
|December 16, 2024
PubMed
Summary

Researchers developed a new skeletal editing platform using diazirines for single-carbon insertion into C-C bonds. This method enables site-selective carbene insertion and rearrangement for molecular 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

9.2K
Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid
07:06

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

Published on: November 15, 2017

11.4K

Related Experiment Videos

Last Updated: Jun 5, 2025

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
12:27

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes

Published on: September 8, 2013

10.8K
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

9.2K
Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid
07:06

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

Published on: November 15, 2017

11.4K

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Traditional methods for modifying carbon-carbon (C-C) bonds are often limited in scope and efficiency.
  • Developing novel strategies for precise skeletal editing is crucial for advancing molecular synthesis.

Purpose of the Study:

  • To introduce a new platform for skeletal editing of single C-C bonds through single-carbon insertion.
  • To demonstrate a method for site-selective carbene insertion and subsequent rearrangement.

Main Methods:

  • Utilized diazirines for the photogeneration of arylchlorocarbenes, acting as carbynoid species.
  • Achieved site-selective carbene insertion into tertiary C-H bonds.
  • Employed a silver salt-promoted Wagner-Meerwein rearrangement for skeletal modification.

Main Results:

  • Successfully demonstrated a skeletal editing strategy based on selective carbyne C-C bond insertion.
  • Showcased six core-to-core conversions on various substrates.
  • Applied the method to linear and cyclic benzylic substrates, alkanes, and late-stage functionalizations.

Conclusions:

  • The developed platform offers a novel approach for C-C bond skeletal editing via single-carbon insertion.
  • This strategy provides a powerful tool for complex molecule synthesis and functionalization.