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Functionalized fluorenes via dicationic electrophiles.

Michael R Stentzel1, Douglas A Klumpp1

  • 1Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, IL 60115, United States.

Tetrahedron Letters
|September 24, 2021
PubMed
Summary

Novel dicationic fluorenyl cations react with nitriles and alcohols to form amide- and ether-functionalized fluorenes, respectively. This chemistry originates from N-heterocyclic ketones in superacidic media, enabling cyclization and cation generation.

Keywords:
CarbocationHeterocycleSuperacidSuperelectrophile

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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry

Background:

  • Dicationic fluorenyl cations are reactive intermediates.
  • N-heterocyclic ketones can be precursors to complex organic structures.

Purpose of the Study:

  • To explore the reactivity of dicationic fluorenyl cations with nucleophiles.
  • To develop a synthetic route to functionalized fluorenes.

Main Methods:

  • Generation of dicationic fluorenyl cations in superacidic solution from N-heterocyclic ketones.
  • Reaction of the cations with nitriles and alcohols.

Main Results:

  • Amide-functionalized fluorenes were synthesized via reaction with nitriles.
  • Ether derivatives of fluorenes were synthesized via reaction with alcohols.
  • The reaction pathway involves cyclization of 2-biphenyl groups.

Conclusions:

  • Dicationic fluorenyl cations offer a versatile platform for synthesizing functionalized fluorenes.
  • The described method provides access to novel amide and ether fluorene derivatives.