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

Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

5.1K
Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
5.1K
Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

6.7K
Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.
6.7K
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

8.1K
Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
8.1K
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

3.4K
Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
3.4K
Acid Halides to Ketones: Gilman Reagent01:14

Acid Halides to Ketones: Gilman Reagent

3.1K
Lithium dialkyl cuprate, also known as Gilman reagents, selectively reduces acid halides to ketones. The acid chloride is treated with Gilman reagent at −78 °C in the presence of ether solution to produce a ketone in good yield.
As shown below, the mechanism proceeds in two steps. First, one of the alkyl groups of the reagent acts as a nucleophile and attacks the acyl carbon of the acid chloride to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen...
3.1K
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

10.8K
Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
10.8K

You might also read

Related Articles

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

Sort by
Same author

Neurophobia in context: Demographic and mental health correlates.

Journal of the neurological sciences·2026
Same author

2M Phase Engineering of W<sub>1-x</sub>Mo<sub>x</sub>S<sub>2</sub> Alloy Nanosheets for Enhanced Catalytic Hydrogen Evolution Reaction.

Small (Weinheim an der Bergstrasse, Germany)·2026
Same author

Unlocking the catalytic role of oxygen functionalities on carbon-based catalysts for hydrogen generation from ammonia borane.

Physical chemistry chemical physics : PCCP·2026
Same author

STEM in an SEM: Towards high-throughput imaging and analysis of metal nanoclusters.

Ultramicroscopy·2026
Same author

Photocatalyzed oxidative cleavage of alkenes using CO<sub>2</sub> as an oxygen donor.

Science (New York, N.Y.)·2026
Same author

Evidence of Local Structural Variations and Their Influence on Magnetic Properties in Mn- and Cr-Containing High-Entropy Oxide Thin Films Using Electron Microscopy.

Journal of the American Chemical Society·2026
Same journal

Fundamentals, Measurement and Regulation of the Conductance of Single Molecule Junctions.

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

Quantitative Photoswitching of Spin States in o-Fluoroazobenzene-Loaded Metal-Organic Frameworks.

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

Cobalt Nanoparticles Confined in Defective Carbon Matrices for Robust Intermittent CO<sub>2</sub> Methanation.

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

Copper(II/III) Redox Couple Enables C─H Methylation via a Radical Mechanism Analogous to SAM Enzymes.

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

Ring Strain Engineering of Cyclic Ethers for High-Performance Sodium Metal Batteries.

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

Bond Length as a Unified Descriptor for Stable Iodine Battery.

Angewandte Chemie (International ed. in English)·2026
See all related articles

Related Experiment Video

Updated: Sep 12, 2025

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
12:30

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework

Published on: April 9, 2018

9.2K

Copper Single-Atom Catalyst for Efficient C─S Coupling in Thioether Synthesis.

Theodore A Gazis1, Shilpa Palit1, Luis A Cipriano1

  • 1Department of Chemistry, Materials, and Chemical Engineering "Giulio Natta", Politecnico di Milano, Piazza Leonardo da Vinci 32, Milano, 20133, Italy.

Angewandte Chemie (International Ed. in English)
|August 6, 2025
PubMed
Summary
This summary is machine-generated.

Researchers developed a recyclable copper single-atom catalyst for efficient carbon-sulfur bond formation. This breakthrough addresses challenges in synthesizing thioethers for pharmaceuticals and materials, offering a greener alternative to traditional methods.

Keywords:
Cross‐coupling reactionsC─S Bond formationDensity functional theoryFine chemical synthesisSingle‐atom catalysis

More Related Videos

[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

9.4K
Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
08:56

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

2.9K

Related Experiment Videos

Last Updated: Sep 12, 2025

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
12:30

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework

Published on: April 9, 2018

9.2K
[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

9.4K
Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
08:56

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

2.9K

Area of Science:

  • Heterogeneous catalysis
  • Materials science
  • Organic synthesis

Background:

  • Carbon-sulfur (C─S) bond formation is crucial for synthesizing thioethers used in pharmaceuticals, agrochemicals, and materials.
  • Current industrial methods for C─S coupling often employ expensive homogeneous catalysts with poor recyclability and susceptibility to sulfur poisoning.
  • Developing efficient, selective, and robust catalysts for C─S cross-coupling remains a significant challenge in synthetic chemistry.

Purpose of the Study:

  • To develop an efficient, selective, and recyclable catalyst for carbon-sulfur (C─S) cross-coupling reactions.
  • To investigate the use of a copper single-atom catalyst supported on mesoporous graphitic carbon nitride for C─S bond formation.
  • To provide mechanistic insights into the catalytic process and demonstrate its applicability on a gram scale under mild conditions.

Main Methods:

  • Synthesis and characterization of a copper single-atom catalyst atomically dispersed on mesoporous graphitic carbon nitride.
  • Testing the catalyst's performance in carbon-sulfur (C─S) cross-coupling reactions under mild conditions.
  • Utilizing advanced characterization techniques (electron microscopy, X-ray absorption spectroscopy, EELS) and computational simulations (DFT) for mechanistic studies.

Main Results:

  • The copper single-atom catalyst demonstrated high efficiency and selectivity in C─S cross-coupling reactions.
  • The catalyst exhibited excellent resistance to thiol poisoning and maintained high performance over multiple catalytic cycles, confirming its recyclability.
  • Mechanistic investigations supported a concerted oxidative addition pathway, ruling out radical intermediates, and confirmed the atomic dispersion and stability of Cu sites.

Conclusions:

  • Atomically dispersed copper on mesoporous graphitic carbon nitride serves as a highly effective heterogeneous catalyst for C─S cross-coupling.
  • This single-atom catalyst approach overcomes limitations of traditional methods, offering enhanced stability, recyclability, and resistance to sulfur poisoning.
  • The findings pave the way for greener, more scalable synthetic processes for fine chemicals and pharmaceuticals utilizing C─S bond formation.