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Updated: Aug 28, 2025

Synthesis and Characterization of Supramolecular Colloids
Published on: April 22, 2016
All That metas─Synthesis of Dispersion Energy Donor-Substituted Benzenes
Lukas Ochmann1, Michael Fuhrmann1, Felix J Gössl1
1Institute of Organic Chemistry, Justus Liebig University, Heinrich-Buff-Ring 17, 35392 Giessen, Germany.
Abstract:
We report a general and scalable method for the synthesis of all-meta-trisubstituted benzenes from readily available 3,5-disubstituted catechols. Oxidation and [4 + 2] cycloaddition with acetylene dienophiles generate a bicyclo[2.2.2]octane structure that is doubly decarbonylated initiated by blue-light irradiation, leading to a meta,meta-disubstitution pattern on the re-aromatized system. This enables this substitution pattern even with very bulky alkyl groups (deemed excellent dispersion energy donors) to be incorporated into, for example, chiral phosphoric acid catalysts.
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