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Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.
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α-Halogenation of aldehydes and ketones is a reaction involving the substitution of α hydrogens with halogens in the presence of a base.  The reaction begins with the abstraction of  α hydrogen by the base to produce a nucleophilic enolate ion. This intermediate undergoes a subsequent nucleophilic substitution with the halogen to produce a monohalogenated carbonyl compound. If the starting substrate has more than one α hydrogen, it is difficult to stop the reaction...
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The thermodynamic favorability of a reaction is determined by the change in Gibbs free energy (ΔG). ΔG has two components- enthalpy (ΔH) and entropy (ΔS). The entropy component is negligible for alkane halogenation because the number of reactants and product molecules are equal. In this case, the ΔG is governed only by the enthalpy component. The most crucial factor that determines ΔH is the strength of the bonds. ΔH can be determined by comparing the energy...
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FON: An Innovative Fluorinated Group via Hydroetherification-Type Reactivity.

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A new method efficiently synthesizes the fluorinated functional group, coined FON, using metal-free reactions. This strategy enables diverse applications, including gram-scale synthesis and deuterium incorporation for medicinal chemistry.

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Area of Science:

  • Organic Chemistry
  • Fluorine Chemistry
  • Medicinal Chemistry

Background:

  • The development of novel fluorinated functional groups is crucial for drug discovery.
  • O-difluoroalkylhydroxylamines (FON) represent a unique structural motif with potential medicinal applications.
  • Existing synthetic routes for such compounds are often limited in scope or efficiency.

Purpose of the Study:

  • To report an efficient, one-step synthesis of the novel O-difluoroalkylhydroxylamine (FON) functional group.
  • To explore the scope and limitations of the developed synthetic methodology.
  • To provide mechanistic insights into the reaction and its potential applications in catalysis.

Main Methods:

  • Metal-free hydroetherification-type addition reactions.
  • Chemo- and regioselective synthesis.
  • Diverse substrate scope evaluation.
  • Gram-scale synthesis and site-selective deuterium incorporation.

Main Results:

  • A novel, efficient one-step synthesis for the FON group was achieved.
  • The reaction demonstrated broad substrate scope and high chemo- and regioselectivity.
  • The method was successfully applied to gram-scale synthesis and site-selective deuterium labeling.
  • Mechanistic studies provided insights into Brønsted acid catalysis.

Conclusions:

  • The reported strategy offers a facile and versatile route to O-difluoroalkylhydroxylamines (FON).
  • This method facilitates the incorporation of FON into diverse molecular architectures.
  • The mechanistic understanding may enable further advancements in fluorination chemistry and catalysis.