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Mechanochemical Scholl Reaction on Phenylated Cyclopentadiene Core: One-Step Synthesis of Fluoreno[5]helicenes. | LitMetric

Mechanochemical Scholl Reaction on Phenylated Cyclopentadiene Core: One-Step Synthesis of Fluoreno[5]helicenes.

Chemistry

School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, 21 Nanyang Link, 637371, Singapore, Singapore.

Published: January 2024

AI Article Synopsis

  • The study investigates the use of a mechanochemical method for synthesizing tetrabenzofluorenes (fluoreno[5]helicenes) using solid-state reactions.
  • The researchers utilized phenylated cyclopentadiene precursors and conducted the Scholl reaction with FeCl as an oxidant and sodium chloride as the reaction medium.
  • The ball milling technique significantly increased the yield of the desired compounds to 95-96%, compared to the lower yields (10-40%) observed in traditional solution-phase reactions.

Article Abstract

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 FeCl 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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Source
http://dx.doi.org/10.1002/chem.202302971DOI Listing

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