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Related Experiment Videos

A Trifluoromethylcarbene Source.

Yaya Duan1, Jin-Hong Lin1, Ji-Chang Xiao1

  • 1Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.

Organic Letters
|May 13, 2016
PubMed
Summary
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A novel method generates trifluoromethylcarbene (:CHCF3) from a sulfonium salt. This carbene is then used in iron-catalyzed cyclopropanation reactions, yielding trifluoromethylated cyclopropanes efficiently.

Area of Science:

  • Organic Chemistry
  • Organometallic Chemistry
  • Fluorine Chemistry

Background:

  • Trifluoromethylated compounds are important in pharmaceuticals and materials science.
  • Efficient generation and application of trifluoromethylcarbene (:CHCF3) remain challenging.

Purpose of the Study:

  • To develop a convenient method for generating trifluoromethylcarbene (:CHCF3).
  • To apply the generated carbene in catalytic cyclopropanation reactions.

Main Methods:

  • Generation of :CHCF3 from (2,2,2-trifluoroethyl)diphenyl-sulfonium triflate.
  • Iron-catalyzed cyclopropanation of various olefins using the generated :CHCF3.

Main Results:

  • The sulfonium salt provides a convenient source for :CHCF3.

Related Experiment Videos

  • High yields of trifluoromethylated cyclopropanes were obtained via Fe-catalyzed reactions.

    • Conclusions:

    • The developed method offers an efficient route to trifluoromethylated cyclopropanes.
    • This approach expands the synthetic utility of trifluoromethylcarbene in organic synthesis.