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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 Friedel–Crafts acylation reactions involve the addition of an acyl group to an aromatic ring. These reactions proceed via electrophilic aromatic substitution by employing an acyl chloride and a Lewis acid catalyst such as aluminum chloride to form aryl ketone.
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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.
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Conversion between difluorocarbene and difluoromethylene ylide.

Jian Zheng1, Jin-Hong Lin, Ji Cai

  • 1Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (P.R. China), Fax: (+86) 21-6416-6128.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|October 12, 2013
PubMed
Summary

Researchers describe the interconversion between difluoromethylene ylide and difluorocarbene. A single precursor can act as either a difluorocarbene reagent or generate a difluoromethylene ylide, enabling selective Wittig difluoro-olefination or difluorocyclopropanation reactions.

Keywords:
carbenesdifluoro-olefinationdifluorocyclopropanationfluorineylides

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Area of Science:

  • Organic Chemistry
  • Organofluorine Chemistry

Background:

  • Difluorocarbene and difluoromethylene ylides are crucial reactive intermediates in organic synthesis.
  • Controlling the selective generation and application of these species remains a synthetic challenge.

Purpose of the Study:

  • To describe the interconversion between difluoromethylene ylide and difluorocarbene.
  • To demonstrate the selective synthesis of difluoro-olefins and difluorocyclopropanes using a single reagent system.

Main Methods:

  • Utilizing a difluoromethylene ylide precursor (Ph3P(+)CF2CO2(-)) as a difluorocarbene source.
  • Employing classical difluorocarbene reagents (HCF2Cl, FSO2CF2CO2TMS) to generate difluoromethylene ylides.
  • Investigating the reactivity of ylides derived from different carbene sources in Wittig reactions.

Main Results:

  • The precursor Ph3P(+)CF2CO2(-) efficiently generates difluorocarbene.
  • Classical difluorocarbene reagents generate highly reactive difluoromethylene ylides.
  • Selective Wittig difluoro-olefination and difluorocyclopropanation are achievable.
  • Ylides from different sources exhibit distinct reactivity in Wittig reactions.

Conclusions:

  • A versatile synthetic strategy for accessing both difluorocarbene and difluoromethylene ylide is established.
  • This approach allows for selective difluoro-olefination and difluorocyclopropanation reactions.
  • The reactivity of difluoromethylene ylides is dependent on their generation method.