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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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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
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The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
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Radical Reactivity: Concentration Effects01:20

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In a radical reaction, the concentration of starting materials governs the selectivity of a radical. For example, the reaction between an alkyl halide and an alkene, in the presence of tin hydride and AIBN, begins with the generation of a tin radical. The generated radical then abstracts halogen from the alkyl halide, producing an alkyl radical. This alkyl radical can either react with tin hydride, yielding an alkane, or add to an alkene, generating a nitrile-stabilized radical, eventually...
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If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
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α-Substituted ketones or aldehydes can be synthesized from enamines by the Stork enamine reaction, named after its pioneer Gilbert Stork. Enamines are useful synthetic intermediates where the lone pair on nitrogen is in conjugation with the C=C bond. They resemble enolate ions, as the resonance forms of both species have a nucleophilic α carbon.
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A Bench-Stable, Single-Component Precatalyst for Silyl-Heck Reactions.

Sarah B Krause1, Jesse R McAtee1, Glenn P A Yap1

  • 1Department of Chemistry and Biochemistry, University of Delaware , Newark, Delaware 19716, United States.

Organic Letters
|September 30, 2017
PubMed
Summary

A new palladium iodide dimer precatalyst, [(JessePhos)PdI2]2, has been identified for the silyl-Heck reaction. This stable, easily prepared complex offers improved activity and reproducibility over existing methods.

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Synthetic Organic Chemistry

Background:

  • The silyl-Heck reaction is a crucial carbon-carbon bond-forming reaction.
  • Identifying efficient and stable palladium precatalysts is key to advancing this methodology.
  • Previous systems often lack optimal activity or reproducibility.

Purpose of the Study:

  • To identify and characterize active palladium species in the silyl-Heck reaction.
  • To develop a novel, single-component precatalyst for enhanced reaction performance.
  • To evaluate the stability, ease of preparation, and catalytic efficiency of the new precatalyst.

Main Methods:

  • In situ generation and spectroscopic identification of palladium complexes.
  • Synthesis and characterization of the [(JessePhos)PdI2]2 dimer.
  • Evaluation of the precatalyst's performance in the silyl-Heck reaction under various conditions.

Main Results:

  • A novel palladium iodide dimer, [(JessePhos)PdI2]2, was identified as the active species.
  • This dimer functions as a competent, single-component precatalyst.
  • The precatalyst demonstrates superior activity and reproducibility compared to prior catalytic systems.
  • The complex exhibits excellent thermal, moisture, and air stability.

Conclusions:

  • The [(JessePhos)PdI2]2 dimer represents a significant advancement in silyl-Heck reaction catalysis.
  • Its stability and ease of preparation make it a practical alternative for synthetic chemists.
  • This discovery facilitates more efficient and reliable synthesis of silyl-substituted alkenes.