Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume -, Issue -, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202302971
Keywords
annulation; arenes; corannulene, fused-ring systems; mechanochemistry
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This study demonstrates the feasibility of the mechanochemical approach in the synthesis of tetrabenzofluorenes. The ball milling process allows for the high-yield, one-step synthesis of the desired product, while the solution-phase reactions have lower yields.
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 %).
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