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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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The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para...
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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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Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
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Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
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Synthetic Strategies to Access Fluorinated Azoles.

Mohammed K Abd El-Gaber1,2, Mario Djugovski1,3, Tzu-Yu Huang1

  • 1Department of Pharmaceutical Sciences, University of Tennessee Health Science Center, Memphis, TN 38103, USA.

European Journal of Organic Chemistry
|December 3, 2025
PubMed
Summary
This summary is machine-generated.

Fluorine incorporation into azoles enhances drug properties like stability and binding. This review details synthetic strategies for fluorinated azoles, crucial for developing new pharmaceuticals.

Keywords:
N-containing heterocyclesdifluoromethylationfluorination strategiesmonofluorinationtrifluoromethylation

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Area of Science:

  • Medicinal Chemistry
  • Organic Synthesis
  • Heterocyclic Chemistry

Background:

  • Fluorine incorporation is vital in medicinal chemistry for optimizing drug properties.
  • Azoles are key heterocyclic scaffolds in drug discovery.
  • Fluorination impacts physicochemical, pharmacokinetic, and pharmacodynamic profiles.

Purpose of the Study:

  • To provide a comprehensive overview of synthetic strategies for fluorinating various azoles.
  • To identify limitations and research gaps in the synthesis of fluorinated azoles.
  • To guide chemists in developing next-generation fluorinated azole pharmaceuticals.

Main Methods:

  • Review of key synthetic strategies for monofluorination, difluoromethylation, and trifluoromethylation.
  • Focus on 11 prominent azole classes.
  • Integration of recent advancements in synthetic methodologies.

Main Results:

  • Detailed overview of established and emerging synthetic routes for fluorinated azoles.
  • Identification of specific challenges and opportunities in current synthetic approaches.
  • Compilation of strategies applicable to a wide range of azole derivatives.

Conclusions:

  • Strategic fluorination of azoles is essential for modern drug development.
  • Further innovation in synthetic methods is needed to overcome current limitations.
  • This review serves as a practical resource and inspiration for medicinal chemists.