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Halogens are ortho–para directors. They are more electronegative than carbon. Therefore, as ring substituents, they can withdraw electrons through the inductive effect and deactivate the aromatic ring towards electrophilic substitution. Halogens also have an electron-donating resonance effect on the ring, which influences the orientation of the incoming electrophile. If an electrophile attacks at the ortho or the para position, the halogen donates electrons and stabilizes the intermediate...
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All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
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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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Decarboxylative Fluorination Catalyzed by Pyridine-Containing Charge-Transfer Complex.

Zhiyang Ma1, Liang Zhang1, Jinglan Wen1

  • 1Institute of Green Chemistry and Molecular Engineering, GBRCE for Functional Molecular Engineering, Lehn Institute of Functional Materials, School of Chemistry, Sun Yat-Sen University, Guangzhou 510006, China.

Organic Letters
|August 20, 2025
PubMed
Summary
This summary is machine-generated.

A new organic photoredox system uses a pyridine-Selectfluor complex for visible-light-driven decarboxylative fluorination of carboxylic acids. This method efficiently converts various alkyl carboxylic acids into valuable fluorinated compounds.

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Area of Science:

  • Organic Chemistry
  • Photoredox Catalysis
  • Fluorination Chemistry

Background:

  • Decarboxylative reactions are crucial for C-C bond formation and functionalization.
  • Photoredox catalysis offers a sustainable approach to organic transformations using visible light.
  • Selective fluorination remains a significant challenge in synthetic chemistry.

Purpose of the Study:

  • To develop a novel photoredox decarboxylation system for the fluorination of alkyl carboxylic acids.
  • To utilize a charge-transfer complex as the catalytic species for enhanced reactivity.
  • To establish a visible-light-mediated protocol applicable to diverse carboxylic acid substrates.

Main Methods:

  • Formation of a charge-transfer complex between pyridine derivatives and Selectfluor.
  • Irradiation with visible light under basic conditions.
  • Application to primary, secondary, and tertiary alkyl carboxylic acids.

Main Results:

  • Successful decarboxylative fluorination of alkyl carboxylic acids.
  • Demonstrated good substrate scope, including primary, secondary, and tertiary substrates.
  • The novel catalytic system operates efficiently under mild conditions.

Conclusions:

  • The developed organic photoredox system provides an effective route for decarboxylative fluorination.
  • The charge-transfer complex approach offers a unique strategy for activating carboxylic acids.
  • This methodology expands the toolkit for introducing fluorine into organic molecules.