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

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

1.5K
The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
1.5K
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview01:19

α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview

1.3K
The pinacol and McMurry reactions involve the reductive coupling of ketones or aldehydes. Similarly, the bimolecular reductive coupling of two ester molecules in the presence of sodium metal in an aprotic solvent yields an α-hydroxy ketone product. The α-hydroxy ketone is also called acyloin, so the reaction is referred to as ‘acyloin condensation.’
1.3K
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

3.2K
By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic...
3.2K
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.4K
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.
2.4K
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

6.2K
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.
6.2K
Sharpless Epoxidation02:57

Sharpless Epoxidation

4.3K
The conversion of allylic alcohols into epoxides using the chiral catalyst was discovered by K. Barry Sharpless and is known as Sharpless epoxidation. The use of a chiral catalyst enables the formation of one enantiomer of the product in excess. This chiral catalyst is mainly a chiral complex of titanium tetraisopropoxide and tartrate ester (specific stereoisomer). The stereoisomer used in the chiral catalyst dictates the formation of the enantiomer of the product. In other words, the use of...
4.3K

You might also read

Related Articles

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

Sort by
Same author

Titanium-Catalyzed Diastereoselective Keto- and Iminonitrile Cyclizations.

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

Discontinuation of immune checkpoint inhibitors for reasons other than disease progression and the impact on relapse and survival of advanced melanoma patients. A systematic review and meta-analysis.

Frontiers in immunology·2025
Same author

Methoxide-Enabled Zirconium-Catalyzed Migratory Alkene Hydrosilylation.

Angewandte Chemie (International ed. in English)·2024
Same author

Clinical efficacy of IgM-enriched immunoglobulin as adjunctive therapy in neonatal and pediatric sepsis: a systematic review and meta-analysis.

Frontiers in pediatrics·2023
Same author

Photoinduced Ring-Opening and Phototoxicity of an Indolin-3-one Derivative.

Chemistry (Weinheim an der Bergstrasse, Germany)·2023
Same author

Catalytic Asymmetric β-Oxygen Elimination.

Angewandte Chemie (International ed. in English)·2022

Related Experiment Video

Updated: May 6, 2026

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
10:12

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Published on: April 4, 2014

12.3K

The cross-selective titanium(III)-catalysed acyloin reaction.

Markus Feurer1, Georg Frey, Hieu-Trinh Luu

  • 1Institut für Organische Chemie, Albert-Ludwigs-Universität Freiburg, Albertstraße 21, 79104 Freiburg, Germany. jan.streuff@ocbc.uni-freiburg.de.

Chemical Communications (Cambridge, England)
|October 19, 2013
PubMed
Summary

A new titanium-catalyzed reaction couples ketones or imines with nitriles, producing valuable α-hydroxylated and α-aminated ketones. This method offers a cross-selective, catalytic alternative to traditional acyloin condensation.

More Related Videos

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

6.6K
Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
11:44

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

Published on: March 20, 2014

25.9K

Related Experiment Videos

Last Updated: May 6, 2026

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
10:12

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Published on: April 4, 2014

12.3K
Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

6.6K
Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
11:44

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

Published on: March 20, 2014

25.9K

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • The classical acyloin condensation is a fundamental organic reaction for forming carbon-carbon bonds.
  • Developing catalytic and selective methods for synthesizing complex organic molecules remains a key challenge in chemistry.

Purpose of the Study:

  • To develop a novel titanium(III)-catalyzed intermolecular reductive coupling reaction.
  • To provide direct access to α-hydroxylated and α-aminated ketones from readily available starting materials.
  • To establish a catalytic and cross-selective alternative to existing synthetic routes.

Main Methods:

  • Utilized titanium(III) as a catalyst for the intermolecular reductive coupling.
  • Employed ketones or imines and nitriles as reaction substrates.
  • Investigated reaction selectivity and scope.
  • Performed Density Functional Theory (DFT) calculations to elucidate the reaction mechanism.

Main Results:

  • Achieved successful titanium(III)-catalyzed intermolecular reductive coupling of ketones/imines with nitriles.
  • Synthesized α-hydroxylated and α-aminated ketones with high efficiency.
  • Demonstrated the cross-selective nature of the coupling reaction.
  • Proposed a reaction mechanism supported by DFT calculations.

Conclusions:

  • The developed titanium-catalyzed reaction provides a novel and efficient route to α-functionalized ketones.
  • This method represents a catalytic advancement over the classical acyloin condensation.
  • The mechanistic insights offer a foundation for further development in reductive coupling strategies.