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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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Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism01:10

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Cyanohydrins are formed when cyanide nucleophiles and carbonyl compounds like aldehydes and ketones react. A strong base, the cyanide ion, catalyzes cyanohydrin formation. The ions are generated from HCN under aqueous conditions. Once the cyanide ions are generated, the first step involves the nucleophilic attack of the cyanide ions on the electrophilic carbonyl carbon. This attack shifts the π electrons from the C=O to the oxygen atom forming the alkoxide ion intermediate. The alkoxide anion...
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Atomic Fluorescence Spectroscopy01:29

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Atomic fluorescence spectroscopy (AFS) is an analytical technique that involves the electronic transitions of atoms in a flame, furnace, or plasma being excited by electromagnetic (EM) radiation. When these atoms absorb energy, they become excited and subsequently release energy as they return to their original state. This emitted light, or "fluorescence," is observed at a right angle to the incident beam. Both absorption and emission processes transpire at distinct wavelengths, which...
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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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Lewis Structures of Molecular Compounds and Polyatomic Ions02:54

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To draw Lewis structures for complicated molecules and molecular ions, it is helpful to follow a step-by-step procedure as outlined:
44.0K
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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Updated: Dec 27, 2025

Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
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Deoxyfluorination with CuF2 : Enabled by Using a Lewis Base Activating Group.

D Eilidh Sood1, Sue Champion2, Daniel M Dawson1

  • 1EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife, KY16 9ST, UK.

Angewandte Chemie (International Ed. in English)
|February 29, 2020
PubMed
Summary
This summary is machine-generated.

Researchers developed a simple deoxyfluorination strategy using first-row transition-metal fluorides, overcoming limitations of low reactivity. This method enables effective nucleophilic fluoride transfer to alcohols and facilitates 18F-radiolabeling.

Keywords:
alcoholscopperfluorineradiolabelingsynthetic methods

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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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Area of Science:

  • Organic Chemistry
  • Fluorination Chemistry
  • Medicinal Chemistry

Background:

  • Deoxyfluorination is crucial for synthesizing organofluorine compounds, essential in pharmaceuticals and materials science.
  • Traditional deoxyfluorination often relies on expensive, bespoke reagents due to the poor reactivity of simple metal fluorides.
  • Developing cost-effective and efficient deoxyfluorination methods using abundant metal fluorides remains a significant challenge.

Purpose of the Study:

  • To develop a simple and efficient deoxyfluorination strategy utilizing readily available first-row transition-metal fluorides.
  • To activate metal fluorides for effective nucleophilic fluoride transfer to alcohols.
  • To explore the application of this method in 18F-radiolabeling for positron emission tomography (PET) imaging.

Main Methods:

  • In situ activation of an O-alkylisourea adduct.
  • Utilizing copper(II) fluoride (CuF2) as a representative first-row transition-metal fluoride.
  • Spectroscopic investigations to elucidate the mechanism and enhanced reactivity of CuF2.

Main Results:

  • A novel deoxyfluorination protocol was established using CuF2, enabling efficient fluoride transfer to primary and secondary alcohols.
  • The O-alkylisourea adduct formation in situ was key to activating the metal fluoride.
  • Spectroscopic studies provided insights into the enhanced reactivity of CuF2 in this transformation.

Conclusions:

  • The developed strategy offers a simple, cost-effective alternative for deoxyfluorination using first-row transition-metal fluorides.
  • This method overcomes the inherent low reactivity issues associated with metal fluorides.
  • The protocol's utility in 18F-radiolabeling demonstrates its potential for synthesizing radiotracers for medical imaging.