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Related Concept Videos

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview01:27

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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.
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Crossed Aldol Reactions: Overview01:04

Crossed Aldol Reactions: Overview

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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.
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Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

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In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
10.3K
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

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2.3K
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.
2.3K
Cycloaddition Reactions: Overview01:16

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3.4K
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.
3.4K
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3.8K
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.
3.8K

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Iron-Catalyzed Cross-Electrophile Coupling.

Julius Semenya1, Yuanjie Yang1, Elias Picazo1

  • 1Department of Chemistry, Loker Hydrocarbon Research Institute, University of Southern California, 837 Bloom Walk, Los Angeles, CA 90089-1661, USA.

Synlett : Accounts and Rapid Communications in Synthetic Organic Chemistry
|September 29, 2025
PubMed
Summary
This summary is machine-generated.

This study introduces an iron-catalyzed cross-electrophile coupling method to synthesize thioethers from benzyl halides and disulfides. The novel approach effectively prevents homodimer formation, offering a significant advancement in organic synthesis.

Keywords:
alkyl halidescross-electrophile couplingdisulfidesiron catalysisthioethers

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Metal-catalyzed cross-coupling reactions are crucial for molecular synthesis.
  • Cross-electrophile coupling reactions are challenging due to side reactions like homodimer formation.

Purpose of the Study:

  • To develop a novel iron-catalyzed method for cross-electrophile coupling.
  • To synthesize thioethers from benzyl halides and disulfides.
  • To overcome the challenge of homodimer formation in these reactions.

Main Methods:

  • Utilized an iron catalyst for cross-electrophile coupling.
  • Employed benzyl halides and disulfides as substrates.
  • Avoided the need for exogenous reductants or photoredox conditions.

Main Results:

  • Successfully synthesized thioethers with high efficiency.
  • Achieved undetectable levels of elimination byproducts.
  • Demonstrated the generality of the developed method.

Conclusions:

  • The developed iron-catalyzed method provides an effective strategy to prevent homodimer formation.
  • This approach offers a new, efficient route for thioether synthesis.
  • The method represents a significant advancement in cross-electrophile coupling reactions.