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

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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.
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...
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
Electrophilic Addition to Alkynes: Hydrohalogenation02:35

Electrophilic Addition to Alkynes: Hydrohalogenation

Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).

You might also read

Related Articles

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

Sort by
Same author

Liquid-Phase CO<b><sub>2</sub></b> Capture by a Nonaqueous Cooperative Absorption Mechanism.

Journal of the American Chemical Society·2026
Same author

Characterization Standard for <i>In-situ</i> Cryo-electron Tomography.

bioRxiv : the preprint server for biology·2026
Same author

Orthogonal Chemistry Enables Precision Nanoparticle Cofunctionalization for Tuning Immune Stimulation and Antigen Presentation.

Biomacromolecules·2026
Same author

Biological evaluation of amidine derivatives: In vitro cytotoxicity and cellular antioxidant capacity.

PloS one·2026
Same author

Tumor agnostic drug delivery with dynamic nanohydrogels.

Nature communications·2026
Same author

Detergents alter the stability and lipid binding properties of the CD1d immunoreceptor.

Protein science : a publication of the Protein Society·2025
Same journal

Reaction Optimization for Enzymatic Deconstruction of Industrially Relevant Nylon Composites.

Chembiochem : a European journal of chemical biology·2026
Same journal

Deploying Artificial Metalloenzymes in Complex Environments: Strategies and Applications.

Chembiochem : a European journal of chemical biology·2026
Same journal

Synthetic Ligands of Myeloid C-Type Lectin Receptors.

Chembiochem : a European journal of chemical biology·2026
Same journal

Vancomycin-Mediated Binding of DNA Origami Nanostructures to Gram-Positive and Gram-Negative Bacteria.

Chembiochem : a European journal of chemical biology·2026
Same journal

Mutasynthesis and Antibiotic Activity of Mupirocin Analogues.

Chembiochem : a European journal of chemical biology·2026
Same journal

Pressure-Dependent Aromatic Ring Flips Reveal Variable Transition-State Volume and Compressibility Among Structural Regions of BPTI.

Chembiochem : a European journal of chemical biology·2026
See all related articles

Related Experiment Video

Updated: Jul 5, 2026

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
09:35

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

Electrochemically protected copper(I)-catalyzed azide-alkyne cycloaddition.

Vu Hong1, Andrew K Udit, Richard A Evans

  • 1Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA. mgfinn@scripps.edu

Chembiochem : a European Journal of Chemical Biology
|May 28, 2008
PubMed
Summary
This summary is machine-generated.

This study introduces an electrochemical method to stabilize air-sensitive copper catalysts for copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reactions. This approach enables high yields in bioconjugation under aerobic conditions without chemical reductants.

More Related Videos

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
12:31

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry

Published on: August 19, 2012

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
11:45

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Published on: August 22, 2018

Related Experiment Videos

Last Updated: Jul 5, 2026

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
09:35

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
12:31

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry

Published on: August 19, 2012

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
11:45

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Published on: August 22, 2018

Area of Science:

  • Chemical Biology
  • Organic Chemistry
  • Electrochemistry

Background:

  • Copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) is vital but requires air-sensitive catalysts.
  • Achieving high yields often necessitates harsh conditions or chemical reductants, limiting applications.

Purpose of the Study:

  • To develop an electrochemical method for stabilizing copper(I) catalysts in the presence of air for CuAAC reactions.
  • To demonstrate efficient bioconjugation using this electrochemically protected catalytic system.

Main Methods:

  • Electrochemical potential was applied to maintain copper catalysts in the active Cu(I) oxidation state.
  • Cyclic voltammetry was used to characterize copper complexes with new ligands.
  • Bioconjugation was performed on bacteriophage Qbeta using electrochemically protected catalysts.

Main Results:

  • The electrochemical method successfully maintained catalyst activity in air, achieving high yields for small-molecule and protein substrates.
  • A new water-soluble TBTA ligand derivative was synthesized and characterized.
  • Complete derivatization of bacteriophage particles was achieved within 12 hours using substoichiometric catalyst amounts.

Conclusions:

  • Electrochemical protection offers a robust and mild alternative to chemical reductants for CuAAC reactions.
  • This method facilitates efficient and sensitive bioconjugation under aerobic conditions.
  • The developed system broadens the applicability of CuAAC in demanding biological and chemical contexts.