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Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

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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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Related Experiment Video

Updated: Jun 8, 2026

Identifying Per- and Polyfluorinated Chemical Species with a Combined Targeted and Non-Targeted-Screening High-Resolution Mass Spectrometry Workflow

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Published on: April 18, 2019

Polyfluorination using IF(5).

Tadahito Fukuhara¹, Shoji Hara

¹Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan.

The Journal of Organic Chemistry

|October 13, 2010

Summary

Researchers developed a new method for polyfluorination of α-(arylthio)carbonyl compounds, introducing three to six fluorine atoms selectively. This advancement in selective fluorination opens new avenues in synthetic chemistry.

Area of Science:

Organic Chemistry
Fluorine Chemistry

Background:

α-(Arylthio)carbonyl compounds are versatile synthetic intermediates.
Selective introduction of multiple fluorine atoms remains a synthetic challenge.

Purpose of the Study:

To develop a novel method for the polyfluorination of α-(arylthio)carbonyl compounds.
To achieve selective introduction of three to six fluorine atoms into specific carbon positions.

Main Methods:

Successive application of polyfluorination using iodine pentafluoride (IF5).
Incorporation of Friedel-Crafts arylation.
Desulfurizing fluorination utilizing IF5.

Main Results:

Selective introduction of three to six fluorine atoms was achieved.

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Fluorine atoms were precisely located on carbons between the aromatic ring and the carbonyl group.

The method offers a new route to polyfluorinated organic compounds.

Conclusions:

A novel and efficient method for polyfluorination of α-(arylthio)carbonyl compounds has been established.
The developed strategy allows for controlled and selective multi-fluorination.
This work expands the toolkit for synthesizing complex fluorinated molecules.