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Related Concept Videos

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

8.1K
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.
8.1K
Halogenation of Alkenes02:46

Halogenation of Alkenes

21.5K
Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
21.5K
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

4.0K
Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
4.0K
Halogens03:01

Halogens

24.3K
Group 17 elements, known as halogens, are nonmetals. At room temperature, fluorine and chlorine are gases, bromine is a liquid, and iodine a solid. Astatine is a highly unstable radioactive element, so currently, most of its properties are unknown due to its short half-life. Tennessine is a synthetic element also predicted to be in this group. 
24.3K
Radical Substitution: Halogenation of Alkanes and Alkyl Substituents01:27

Radical Substitution: Halogenation of Alkanes and Alkyl Substituents

10.6K
In the presence of heat or light, alkanes react with molecular halogens to form alkyl halides by a substitution reaction called radical halogenation. This reaction has three steps: initiation, propagation, and termination, as seen in the radical chlorination of methane to produce methyl chloride.
In the initiation step of the reaction, the chlorine molecule undergoes homolytic cleavage in the presence of light or heat, forming two highly reactive chlorine radicals. Propagation occurs in two...
10.6K
ortho–para-Directing Deactivators: Halogens01:24

ortho–para-Directing Deactivators: Halogens

7.2K
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...
7.2K

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Related Experiment Video

Updated: Apr 16, 2026

Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
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Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes

Published on: July 28, 2018

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Direct fluorination of styrenes.

Qian Shao1, Yong Huang

  • 1Key Laboratory of Chemical Genomics, Peking University, Shenzhen Graduate School, Shenzhen, 518055 China. huangyong@pkusz.edu.cn.

Chemical Communications (Cambridge, England)
|March 17, 2015
PubMed
Summary

Researchers created a straightforward method for synthesizing fluorostyrene compounds. This involves a mild, regioselective mono-fluorination of styrenes using ruthenium(III) chloride and N-fluorobenzenesulfonimide, plus a tandem reaction with gold catalysis.

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Fluorine Chemistry

Background:

  • Fluorostyrene derivatives are valuable building blocks in organic synthesis.
  • Efficient and regioselective methods for their preparation are highly sought after.
  • Existing methods may lack generality or require harsh conditions.

Purpose of the Study:

  • To develop a practical and mild method for synthesizing fluorostyrene compounds.
  • To achieve regioselective mono-fluorination of diverse styrene substrates.
  • To explore a tandem reaction combining alkyne hydroarylation and olefin fluorination.

Main Methods:

  • Utilized ruthenium(III) chloride (RuCl3) as a catalyst for fluorination.
  • Employed N-fluorobenzenesulfonimide (NFSI) as the fluorine source.

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Preparation of Hollow Polystyrene Particles and Microcapsules by Radical Polymerization of Janus Droplets Consisting of Hydrocarbon and Fluorocarbon Oils
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Preparation of Hollow Polystyrene Particles and Microcapsules by Radical Polymerization of Janus Droplets Consisting of Hydrocarbon and Fluorocarbon Oils

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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

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Last Updated: Apr 16, 2026

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Preparation of Hollow Polystyrene Particles and Microcapsules by Radical Polymerization of Janus Droplets Consisting of Hydrocarbon and Fluorocarbon Oils
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Preparation of Hollow Polystyrene Particles and Microcapsules by Radical Polymerization of Janus Droplets Consisting of Hydrocarbon and Fluorocarbon Oils

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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

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  • Developed a gold (Au) catalyzed tandem reaction for sequential hydroarylation and fluorination.

    • Main Results:

    • Achieved smooth and regioselective mono-fluorination of various di- and trisubstituted styrenes.
    • Demonstrated the efficacy of the RuCl3/NFSI system under mild conditions.
    • Successfully developed a tandem alkyne hydroarylation-olefin fluorination sequence using an Au catalyst.

    Conclusions:

    • The developed method provides a practical route to valuable fluorostyrene compounds.
    • The regioselectivity and mild conditions offer advantages over existing synthetic strategies.
    • The tandem reaction expands the synthetic utility for accessing complex fluorinated molecules.