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

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

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.
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

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.
β-Dicarbonyl Compounds via Crossed Claisen Condensations01:18

β-Dicarbonyl Compounds via Crossed Claisen Condensations

Crossed Claisen condensations are base-promoted reactions between two different ester molecules producing β-dicarbonyl compounds. The reaction involving esters, with both containing α hydrogen, results in a mixture of four different products that are difficult to isolate. This reduces the synthetic utility of the reaction.
Pericyclic Reactions: Introduction01:17

Pericyclic Reactions: Introduction

Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic rearrangements are...

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Related Experiment Video

Updated: May 7, 2026

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions
11:44

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

Published on: March 20, 2014

Efficient chromium(II)-catalyzed cross-coupling reactions between Csp2 centers.

Andreas K Steib1, Olesya M Kuzmina, Sarah Fernandez

  • 1Department of Chemistry, Ludwig-Maximilians-Universität , Butenandtstrasse 5-13, 81377 Munich, Germany.

Journal of the American Chemical Society
|September 24, 2013
PubMed
Summary

Low-toxicity chromium(II) chloride efficiently catalyzes cross-coupling reactions at room temperature. This method offers a greener alternative with significantly reduced side products compared to other metal catalysts.

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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

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

Published on: April 4, 2014

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Last Updated: May 7, 2026

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions
11:44

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

Published on: March 20, 2014

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Published on: May 26, 2019

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

Area of Science:

  • Organic Chemistry
  • Organometallic Chemistry
  • Catalysis

Background:

  • Cross-coupling reactions are vital for forming carbon-carbon bonds in organic synthesis.
  • Traditional cross-coupling often employs toxic or expensive metals, with side reactions impacting yield.
  • Developing efficient and selective catalysts remains a key challenge in synthetic chemistry.

Purpose of the Study:

  • To investigate the catalytic activity of low-toxicity chromium(II) chloride in cross-coupling reactions.
  • To explore the scope of this catalytic system with various organic substrates.
  • To compare the efficiency and selectivity of chromium-catalyzed coupling against other transition metals.

Main Methods:

  • Utilizing chromium(II) chloride as a catalyst for cross-coupling reactions.
  • Employing (hetero)arylmagnesium reagents with N-heterocyclic halides, aromatic halogenated ketones/imines, and alkenyl iodides.
  • Conducting reactions at 25 °C and analyzing product yields and side product formation.

Main Results:

  • Chromium(II) chloride effectively catalyzed coupling reactions within minutes at room temperature.
  • The catalyst demonstrated broad substrate scope, coupling diverse (hetero)arylmagnesium reagents with various electrophiles.
  • Significantly lower amounts of homo-coupling side products were observed compared to iron, cobalt, or manganese catalysts.

Conclusions:

  • Low-toxicity chromium(II) chloride is a highly effective catalyst for various cross-coupling reactions.
  • This method provides a more selective and potentially greener alternative to existing transition metal-catalyzed couplings.
  • The reduced homo-coupling offers improved synthetic efficiency and atom economy.