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Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
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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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Sulfonation of benzene is a reaction wherein benzene is treated with fuming sulfuric acid at room temperature to produce benzenesulfonic acid. Fuming sulfuric acid is a mixture of sulfur trioxide and concentrated sulfuric acid.
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Hybridization of Atomic Orbitals I03:24

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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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Benzylic C(sp3)-H fluorination.

Alexander P Atkins1, Alice C Dean1, Alastair J J Lennox1

  • 1University of Bristol, School of Chemistry, Bristol, BS8 1TS, U.K.

Beilstein Journal of Organic Chemistry
|July 17, 2024
PubMed
Summary
This summary is machine-generated.

Selective fluorination of C(sp3)-H bonds is crucial for drug and agrochemical development. This review highlights various strategies and mechanisms for achieving selective benzylic C-H bond fluorination.

Keywords:
C–H functionalizationbenzylicfluorinationphotoredox catalysis

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Fluorine Chemistry

Background:

  • Selective fluorination of C(sp3)-H bonds is highly desirable for creating novel pharmaceuticals and agrochemicals.
  • Benzylic C(sp3)-H bonds are particularly important targets due to their prevalence in bioactive molecules.

Purpose of the Study:

  • To provide context and overview of recent advancements in selective C(sp3)-H fluorination.
  • To highlight diverse strategies and mechanistic pathways for benzylic C-H fluorination.

Main Methods:

  • Review of existing literature on C(sp3)-H fluorination methods.
  • Categorization of protocols based on mechanistic pathways.
  • Analysis of various fluorine sources and their reactivity profiles.

Main Results:

  • Several selective methods for benzylic C(sp3)-H fluorination have been reported.
  • These methods utilize distinct mechanistic approaches.
  • A variety of fluorine sources with different reactivity are employed.

Conclusions:

  • The selective fluorination of benzylic C(sp3)-H bonds is an active area of research.
  • Understanding the different tactics is key to advancing the field.
  • Continued development is expected to yield new applications in medicine and agriculture.