Aromatic compounds are often prepared using Lewis acid catalysts and other reagents that are difficult to remove or separate from the desired products at the end of the reaction and also result in the considerable generation of waste. We have developed novel and very useful gel-like reagents that contains both the catalyst and alkyl or alkoxy groups that can be transferred to aromatic rings via electrophilic substitution. Furthermore, the used reagents are insoluble in organic solvents and is readily separated from reaction mixtures. The reagents are salts of lanthanum dialkyl and monoalkyl phosphates and they produce a variety of alkylated and alkoxylated compounds when reacted with toluene. Oxidation of toluene to produce benzaldehyde is also observed and this may play a role in the production of other aromatic derivatives. Remarkably, it was found that the parent alkyl phosphates also work as alkylating agents for aromatic substrates. Such reactions may form the basis for cleaner derivatization reactions for aromatic compounds and the preparation of unusual or difficult to prepare compounds.

Derivatization of aromatic compounds by lanthanum-catalyzed reactions with mono- and dialkylphosphate esters

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.