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Carbonylation of Polyfluorinated 1-Arylalkan-1-ols and Diols in Superacids. | LitMetric

AI Article Synopsis

  • The study focuses on carbonylation reactions involving mono and dihydroxy polyfluorinated alkylbenzenes and benzocycloalkenes, utilizing carbon monoxide and superacids like TfOH and mixtures of FSOH and SbF.
  • It demonstrates that superacid-catalyzed reactions efficiently convert polyfluorinated alcohols and diols into mono- and dicarboxylic acids or lactones, with FSOH-SbF showing the best results for most reactions.
  • Additionally, the findings highlight that secondary alcohols can produce unsaturated aryl-carboxylic acids while tertiary alcohols convert less effectively and lead to decarboxylation post-reaction.

Article Abstract

We describe the carbonylation of a series of mono and dihydroxy derivatives of polyfluorinated alkylbenzenes and benzocycloalkenes with OH groups at benzylic positions using carbon monoxide in the presence of a superacid (TfOH, a TfOH-SbF mixture, or a FSOH-SbF mixture). It was shown that the superacid-catalyzed addition of CO to various primary and secondary polyfluorinated alcohols and diols gives the corresponding mono- and dicarboxylic acids or lactones. The efficiency of various superacids depending on alcohol structure was evaluated, and FSOH-SbF yielded the best results in most transformations. The addition of CO to secondary 1-arylalkan-1-ols containing vicinal fluorine atoms was found to be accompanied by elimination of HF with the formation of -unsaturated aryl-carboxylic acids. In contrast to primary and secondary alcohols, conversion of tertiary perfluoro-1,1-diarylalkan-1-ols into carbonylation products is not complete, and the resulting carboxylic acids are easily decarboxylated after water treatment of the reaction mixture.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9787639PMC
http://dx.doi.org/10.3390/molecules27248757DOI Listing

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