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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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Radical reactions can occur either intermolecularly or intramolecularly. In an intermolecular radical reaction, a nucleophilic radical adds to an electrophilic alkene or vice versa. In such reactions, the radical and generally the alkene, which is also called the radical trap, are two different molecules. Additionally, for such intermolecular reactions to occur, the radical trap must be active, present in an excess concentration, and the radical starting material must have a weak...
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Total Internal Reflection Fluorescence Microscopy01:05

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Total internal reflection fluorescence microscopy or TIRF is an advanced microscopic technique used to visualize fluorophores in samples close to a solid surface with a higher refractive index, such as a glass coverslip. TIRF only allows fluorophores in proximity to the solid surface to be excited. When light from a medium with a lower refractive index (such as air) hits the glass coverslip at a critical angle, the light undergoes total internal reflection stead of passing through the glass.
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Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

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Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
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The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the...
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Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

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Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
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Intramolecular Fluoroacylation Enabled by TrBF4-Catalyzed Fluoride Recycling.

Ali McKnight1, Yuriko H Fujisato1, Namrata Khanal2

  • 1Department of Chemistry, York University, Toronto, Ontario M3J 1P3, Canada.

Organic Letters
|January 27, 2025
PubMed
Summary

This study introduces a new method for synthesizing fluorinated organic compounds using catalytic TrBF4. The process efficiently recycles fluoride, creating novel fluorinated ketones and alkyl fluorides with high stereoselectivity.

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Area of Science:

  • Organic Chemistry
  • Fluorine Chemistry
  • Catalysis

Background:

  • Intramolecular carbofluorination is a key transformation for accessing fluorinated molecules.
  • Existing methods often rely on expensive metal catalysts and harsh reaction conditions.
  • Developing efficient and selective methods for C-F bond formation remains a significant challenge.

Purpose of the Study:

  • To develop a novel catalytic system for intramolecular carbofluorination.
  • To achieve high stereoselectivity in the synthesis of fluorinated cyclic compounds.
  • To provide a more sustainable and cost-effective alternative to existing protocols.

Main Methods:

  • Utilized alkyne- and alkene-tethered acyl fluorides as substrates.
  • Employed catalytic amounts of TrBF4 (Scandium triflate) for fluoride recycling.
  • Investigated the stereoselectivity of the carbofluorination reaction.

Main Results:

  • Achieved efficient intramolecular carbofluorination via fluoride recycling.
  • Demonstrated excellent stereoselectivity for alkyne additions, yielding fluorinated indan-2-ones (≥95:5 E/Z) and cyclopentan-2-ones (85:15 E/Z).
  • Successfully synthesized fluorinated chroman-2-ones and tertiary alkyl fluorides.

Conclusions:

  • The developed TrBF4-catalyzed method offers a highly stereoselective and efficient route to valuable fluorinated compounds.
  • This protocol provides a greener and more economical alternative compared to traditional methods.
  • The fluoride recycling strategy enhances sustainability and reduces catalyst loading.