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Related Concept Videos

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

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Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
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Nucleophilic Aromatic Substitution: Elimination–Addition01:11

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Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
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Elimination Reactions02:25

Elimination Reactions

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A nucleophile can react with an alkyl halide to give the substitution product by displacing the halogen. Or it can function as a base to give the elimination product by deprotonation of the neighboring carbon to form an alkene. In an elimination reaction, the substrate loses two groups from adjacent carbons forming at least one π bond. The carbon attached to the halogen is called the α carbon, while the adjacent carbon is called the β carbon; hence, these reactions are called...
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Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

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Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...
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E2 Reaction: Stereochemistry and Regiochemistry02:43

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Elimination reactions of alkyl halides can yield one or more alkenes depending on the specific regiochemical and stereochemical considerations. While the regiochemistry of the reaction governs the location of the double bond in the product, the stereochemical requirements often influence the geometry.
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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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Related Experiment Video

Updated: Apr 9, 2026

Amide Coupling Reaction for the Synthesis of Bispyridine-based Ligands and Their Complexation to Platinum as Dinuclear Anticancer Agents
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Selective aryl-fluoride reductive elimination from a platinum(IV) complex.

Ina Dubinsky-Davidchik1, Israel Goldberg1, Arkadi Vigalok2

  • 1School of Chemistry, The Sackler Faculty of Exact Sciences, Tel Aviv University, Tel Aviv 69978 (Israel).

Angewandte Chemie (International Ed. in English)
|June 23, 2015
PubMed
Summary
This summary is machine-generated.

A platinum(IV) complex selectively eliminates 2-fluoromesitylene when heated. This C-F bond formation involves a transient five-coordinate platinum(IV) intermediate, driven by pyridine ligand dissociation.

Keywords:
chemoselectivityelectrophilic fluorinationplatinumreaction mechanismsreductive elimination

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Reaction Mechanisms

Background:

  • Platinum(IV) complexes are versatile precursors in catalysis.
  • Reductive elimination is a key step in many catalytic cycles.
  • Understanding C-F bond activation is crucial for synthetic chemistry.

Purpose of the Study:

  • To investigate the mechanism of reductive elimination from a difluoro(mesityl)platinum(IV) complex.
  • To elucidate the role of transient intermediates in C-F coupling reactions.
  • To determine the factors controlling the selectivity of the elimination process.

Main Methods:

  • Synthesis and characterization of the platinum(IV) complex.
  • Thermal reaction studies in toluene.
  • Kinetic analysis of the reductive elimination.
  • Density Functional Theory (DFT) calculations.

Main Results:

  • Highly selective reductive elimination of 2-fluoromesitylene was observed.
  • Kinetic data indicate a rate-limiting dissociation of the pyridine ligand.
  • DFT calculations support a mechanism involving a five-coordinate Pt(IV) intermediate.

Conclusions:

  • The C-F coupling proceeds via a dissociative pathway.
  • Pyridine ligand lability plays a critical role in initiating the reaction.
  • This study provides insights into the reactivity of Pt(IV) complexes in C-F bond functionalization.