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Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

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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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Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
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The mathematical expression known as the wave function, ψ, contains information about each orbital and the wavelike properties of electrons in an isolated atom. When atoms are bound together in a molecule, the wave functions combine to produce new mathematical descriptions that have different shapes. This process of combining the wave functions for atomic orbitals is called hybridization and is mathematically accomplished by the linear combination of atomic orbitals. The new orbitals that...
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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
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C-F Bond Insertion: An Emerging Strategy for Constructing Fluorinated Molecules.

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Chemistry (Weinheim an Der Bergstrasse, Germany)
|January 25, 2024
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Carbon-fluorine (C-F) insertion reactions enable efficient synthesis of fluorinated molecules. Recent advances overcome C-F bond strength challenges, allowing fluoride incorporation into products.

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Area of Science:

  • Organic Chemistry
  • Fluorination Chemistry

Background:

  • Carbon-fluorine (C-F) bonds are strong and difficult to cleave.
  • C-F insertion reactions are attractive for synthesizing fluorinated compounds but are underexplored.
  • Fluoride sequestration in by-products often hinders C-F bond activation.

Purpose of the Study:

  • To review recent breakthroughs in C-F insertion reactions.
  • To highlight conceptual advances enabling C-F bond cleavage and fluoride incorporation.
  • To discuss the efficiency and atom economy of these methods.

Main Methods:

  • Review of recent literature on C-F insertion reactions.
  • Analysis of key conceptual advances in C-F bond activation.
  • Discussion of strategies for fluoride incorporation into products.

Main Results:

  • Several groups have successfully developed methods for C-F insertion.
  • Key advances have enabled overcoming the thermodynamic challenge of C-F bond cleavage.
  • Efficient and atom-economical synthesis of fluorinated molecules is now achievable.

Conclusions:

  • C-F insertion reactions are emerging as powerful tools in synthetic chemistry.
  • Overcoming C-F bond inertness opens new avenues for fluorinated molecule preparation.
  • These methods offer efficient and sustainable routes to valuable fluorinated compounds.