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

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

13.7K
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.
13.7K
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

8.2K
Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
8.2K
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

4.1K
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...
4.1K
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

22.0K
Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
22.0K
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

9.6K
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.
9.6K
Preparation of Epoxides03:00

Preparation of Epoxides

9.9K
Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
9.9K

You might also read

Related Articles

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

Sort by
Same author

A Molecular Analogue of Cu/ZSM‑5 Catalyzing the Monooxygenation of Hydrocarbons via a Mono μ‑Oxo Dicopper Species.

ACS omega·2026
Same author

Synthesis and crystal structure of di-μ-chlorido-bis-[bis(2,6-di-methyl-pyrazine)-copper(I)] and di-μ-bromido-bis[bis(2,6-di-methyl-pyrazine)copper(I)].

Acta crystallographica. Section E, Crystallographic communications·2026
Same author

Synthesis and crystal structure of <i>catena</i>-poly[[[aqua-(2,3-di-methyl-pyrazine-κ<i>N</i>)cadmium(II)]-di-μ-bromido] 2,3-di-methyl-pyrazine monosolvate hemihydrate].

Acta crystallographica. Section E, Crystallographic communications·2026
Same author

Synthesis, crystal structure and thermal properties of di-aqua-bis-(4-cyano-pyridine)-dithiocyanato-nickel(II).

Acta crystallographica. Section E, Crystallographic communications·2026
Same author

Disentangling anisotropy and exchange in Co(NCX)<sub>2</sub> (X = S, Se) chains <i>via</i> THz-EPR spectroscopy.

Dalton transactions (Cambridge, England : 2003)·2026
Same author

Synthesis of a rhenium(VII) trioxo complex supported by a triphyrin ligand: oxygenation chemistry and deposition on Au(111).

Dalton transactions (Cambridge, England : 2003)·2026

Related Experiment Video

Updated: Apr 9, 2026

[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

10.0K

Selective Aromatic Hydroxylation with Dioxygen and Simple Copper Imine Complexes.

Jonathan Becker1, Puneet Gupta2,3, Friedrich Angersbach4

  • 1Institut für Anorganische und Analytische Chemie, Justus-Liebig-Universität Gießen, Heinrich-Buff-Ring 58, 35392 Gießen (Germany).

Chemistry (Weinheim an Der Bergstrasse, Germany)
|June 20, 2015
PubMed
Summary

This study reinvestigates copper imine complexes for selective aromatic aldehyde hydroxylation using dioxygen. A new facile synthetic route introduces hydroxyl groups into aromatic aldehydes via a bis-μ-oxido copper intermediate.

Keywords:
aldehydescopperdensity functional calculationshydroxylationtransition states

More Related Videos

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
09:54

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

Published on: September 12, 2018

8.3K
Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
06:34

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Published on: June 20, 2014

14.5K

Related Experiment Videos

Last Updated: Apr 9, 2026

[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

10.0K
Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
09:54

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

Published on: September 12, 2018

8.3K
Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
06:34

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Published on: June 20, 2014

14.5K

Area of Science:

  • Coordination Chemistry
  • Organic Synthesis
  • Computational Chemistry

Background:

  • Bis(μ-oxido)dicopper complexes are known catalysts for hydroxylation reactions.
  • Previous studies explored the hydroxylation of phenylpyridine ligands by copper complexes.
  • Understanding these catalytic systems is crucial for developing new synthetic applications.

Purpose of the Study:

  • To reinvestigate the bis(μ-oxido)dicopper complex system for improved understanding.
  • To develop a simple copper imine complex for selective aromatic aldehyde hydroxylation.
  • To elucidate the reaction mechanism using computational methods.

Main Methods:

  • Preparation of copper imine complexes with N'-benzylidene-N,N-diethylethylenediamine (BDED) ligand.
  • Selective o-hydroxylation of aromatic aldehydes using dioxygen as the oxidant.
  • Density functional theory (DFT) calculations at the BLYP-D/TZVP level to study reaction mechanisms.

Main Results:

  • Selective o-hydroxylation of aromatic aldehydes was achieved using a copper-BDED complex and dioxygen.
  • Salicylaldehyde was synthesized in good yields, indicating the efficiency of the method.
  • The reaction proceeds through a bis-μ-oxido copper intermediate, similar to previously studied systems.
  • DFT calculations revealed a closely related mechanistic scenario for the BDED-supported complex.

Conclusions:

  • A new, facile synthetic method for introducing hydroxyl groups into aromatic aldehydes has been demonstrated.
  • The copper-catalyzed hydroxylation mechanism involves a bis-μ-oxido copper intermediate.
  • This work provides insights into the development of novel synthetic applications for copper imine complexes.