Mechanochemical Scholl Reaction on Phenylated Cyclopentadiene Core: One‐Step Synthesis of Fluorenohelicenes

In this study, we explore feasibility of the mechanochemical approach in the synthesis of tetrabenzofluorenes (fluoreno[5]helicenes). For this, commercially available phenylated cyclopentadiene precursors are subjected to the Scholl reaction in the solid state using FeCl3 as an oxidant and sodium ch...

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Bibliographic Details
Published in:Chemistry : a European journal 2024-01, Vol.30 (1)
Main Authors: Báti, Gábor, Csókás, Dániel, Stuparu, Mihaiela C
Format: Article
Language:English
Subjects:
Ball milling
Chemistry
Cyclopentadiene
Feasibility studies
Ferric chloride
Oxidants
Oxidizing agents
Sodium chloride
Synthesis
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Summary:In this study, we explore feasibility of the mechanochemical approach in the synthesis of tetrabenzofluorenes (fluoreno[5]helicenes). For this, commercially available phenylated cyclopentadiene precursors are subjected to the Scholl reaction in the solid state using FeCl3 as an oxidant and sodium chloride as the solid reaction medium. This ball milling process gave access to the 5‐membered ring containing‐helicenes in one synthetic step in high (95–96 %) isolated yields. The solution‐phase reactions, however, were found to be moderate to low yielding in this regard (10–40 %).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.202302971