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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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Ziegler–Natta polymerization is another form of addition or chain‐growth polymerization used for synthesizing linear polymers over branched polymers. The catalyst used for polymerization is the Ziegler–Natta catalyst, named after Karl Ziegler and Giulio Natta, who developed it in 1953. This catalyst is an organometallic complex of titanium tetrachloride and triethyl aluminum, with the active form of the catalyst being an alkyl titanium compound. Using the Ziegler–Natta...
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Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

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Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.
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Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

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Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
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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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Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

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A palladium thiolate-SNS complex-catalyst for Mizoroki-Heck cross-coupling.

Saeed Ataie1, Atousa Khanzadeh1, R Tom Baker1

  • 1Department of Chemistry and Biomolecular Sciences and Centre for Catalysis Research and Innovation, University of Ottawa, Ottawa, Ontario K1N 6N5, Canada. rbaker@uottawa.ca.

Dalton Transactions (Cambridge, England : 2003)
|May 9, 2025
PubMed
Summary

New phosphine-free palladium catalysts for Mizoroki-Heck couplings show promise. One complex, Pd-2, is highly active and stable, while Pd-1 is inactive due to structural changes.

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Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Synthetic Chemistry

Background:

  • Mizoroki-Heck cross-coupling reactions are vital in organic synthesis.
  • Phosphine ligands in palladium catalysts can be air and moisture sensitive.
  • Developing phosphine-free alternatives enhances catalyst stability and handling.

Purpose of the Study:

  • To synthesize and evaluate novel phosphine-free palladium(II) complexes for Mizoroki-Heck catalysis.
  • To compare the catalytic activity and stability of two SNS pincer ligand-based complexes.
  • To investigate the deactivation pathway of an inactive palladium complex.

Main Methods:

  • Synthesis of two palladium(II) complexes, Pd(κ²-SNSMe)₂ (Pd-1) and PdI(κ³-SNSMe) (Pd-2), featuring a thiolate-imine-thioether SNS pincer ligand.
  • Comparative catalytic testing of Pd-1 and Pd-2 in Mizoroki-Heck cross-coupling reactions.
  • Structural analysis and investigation of catalyst deactivation pathways under reaction conditions.

Main Results:

  • Pd-2 exhibited excellent catalytic activity in Mizoroki-Heck reactions, achieving high yields with low catalyst loading (1.5 mol%) and short reaction times (5 hours) across diverse substrates.
  • Pd-1 demonstrated no catalytic activity, undergoing isomerization to a Pd(II)-N₂S₂ complex via imine C-C bond formation at elevated temperatures.
  • Heating Pd-2 with excess triethylamine led to selective C-S bond activation, forming a palladium dithiolate tetramer, [Pd(μ-κ³-SNS)]₄.

Conclusions:

  • The SNS pincer ligand effectively stabilizes palladium complexes for Mizoroki-Heck catalysis.
  • Pd-2 represents a highly active and robust phosphine-free catalyst for cross-coupling reactions.
  • Understanding catalyst deactivation mechanisms, such as isomerization and C-S bond activation, is crucial for catalyst design.