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Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

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Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
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Cycloaddition Reactions: Overview01:16

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

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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.
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Crossed Aldol Reactions: Overview01:04

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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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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 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.
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Related Experiment Video

Updated: May 12, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Gold-Catalyzed Deallylative C-S Cross-Coupling Reactions.

Prafulla Bera1, Tanmayee Nanda1, Nayan A Barhate1

  • 1Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhauri 462 066, India.

Organic Letters
|May 1, 2025
PubMed
Summary
This summary is machine-generated.

This study introduces a novel gold-catalyzed deallylative C-S cross-coupling using a ligand-enabled Au(I)/Au(III) redox cycle. Allyl phenyl sulfide acts as a sulfur surrogate, preventing catalyst deactivation and enabling efficient coupling reactions.

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Synthetic Organic Chemistry

Background:

  • Gold catalysis is crucial for C-S bond formation.
  • Catalyst deactivation via gold-sulfur bond formation is a significant challenge.

Purpose of the Study:

  • To develop a gold-catalyzed deallylative C-S cross-coupling reaction.
  • To overcome catalyst deactivation in gold-catalyzed C-S coupling.

Main Methods:

  • Ligand-enabled Au(I)/Au(III) redox catalysis.
  • Utilizing allyl phenyl sulfide as a sulfur surrogate.
  • Mechanistic studies including 31P NMR, mass analysis, and computational modeling.

Main Results:

  • Successful deallylative C-S cross-coupling reaction.
  • Allyl phenyl sulfide facilitates a dynamic equilibrium, preventing gold catalyst quenching.
  • Detailed mechanistic insights were obtained.

Conclusions:

  • The developed method offers an efficient approach to C-S cross-coupling.
  • The use of allyl phenyl sulfide is key to overcoming catalyst deactivation.
  • The study provides a robust understanding of the reaction mechanism.