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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.
Reactions at the Benzylic Position: Oxidation and Reduction00:59

Reactions at the Benzylic Position: Oxidation and Reduction

The benzylic position describes the position of a carbon atom attached directly to a benzene ring. Benzene by itself does not undergo oxidation. In contrast, the benzylic carbon is quite reactive in the presence of strong oxidizing agents such as KMnO4 or H2CrO4. Therefore, alkylbenzenes are readily oxidized to benzoic acid, irrespective of the type of alkyl groups.
Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview01:27

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview

Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.
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.
Crossed Aldol Reactions: Overview01:04

Crossed Aldol Reactions: Overview

Crossed aldol addition is the reaction between two different carbonyl compounds under acidic or basic conditions. Here, both the carbonyl compounds function as nucleophiles and electrophiles. As shown in Figure 1, such a reaction yields a mixture of products, two of which are formed via self-condensation, while the remaining two are formed via crossed-condensation. Without adjustment, the reaction's usefulness in organic chemistry is decreased.
Phase I Reactions: Reductive Reactions01:27

Phase I Reactions: Reductive Reactions

Phase I biotransformation reductive reactions are chemical processes that modify drugs by introducing or revealing polar functional groups via reduction. Enzymes called reductases catalyze these reactions, playing a pivotal role in drug metabolism by transforming lipophilic drugs into more polar, water-soluble metabolites for easy excretion. An essential type of reductive reaction is the carbonyl group reduction, where aldehydes and ketones are reduced to alcohols. An example is the...

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Updated: May 8, 2026

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
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Cobalt-catalyzed reductive cross-coupling: a review.

Shamoon Hassan1, Muhammad Bilal1,2, Shehla Khalid1

  • 1Department of Chemistry, Government College University, Faisalabad, 38000, Pakistan.

Molecular Diversity
|October 28, 2024
PubMed
Summary
This summary is machine-generated.

Cobalt-catalyzed reductive cross-coupling offers an affordable pathway for C-C bond formation. Ongoing research aims to enhance cobalt

Keywords:
Cobalt-catalyzedC–C couplingC–X couplingReductive cross-couplingTransition-metal

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Chemistry

Background:

  • Transition-metal catalysis is crucial for efficient carbon-carbon (C-C) bond formation.
  • Reductive cross-coupling reactions enable the synthesis of diverse C-C bonds with various hybridizations (sp, sp2, sp3).
  • Cobalt offers a cost-effective alternative to palladium and nickel but faces efficacy challenges in catalysis.

Purpose of the Study:

  • To provide an in-depth review of cobalt-catalyzed reductive cross-coupling reactions.
  • To highlight the potential of cobalt catalysis in synthesizing C-C bonds with different hybridizations.
  • To discuss the challenges and future prospects of cobalt in cross-coupling reactions.

Main Methods:

  • Review of existing literature on transition-metal-catalyzed reductive cross-coupling.
  • Focus on studies utilizing cobalt as the primary catalyst.
  • Analysis of substrate scope and product diversity in cobalt-mediated reactions.

Main Results:

  • Cobalt catalysis enables the coupling of unreactive electrophilic substrates.
  • Successful synthesis of C-C bonds with sp, sp2, and sp3 hybridizations using cobalt.
  • Demonstration of cobalt's utility in late-stage functionalization and bioactive molecule synthesis.

Conclusions:

  • Cobalt-catalyzed reductive cross-coupling is a promising and cost-effective method for C-C bond formation.
  • Further research is needed to overcome efficacy challenges and fully harness cobalt's catalytic potential.
  • Cobalt catalysis is poised to revolutionize industrial applications due to its affordability and efficiency.