Carbonylation of Polyfluorinated 1-Arylalkan-1-ols and Diols in Superacids

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 FSO H-SbF mixture). It was shown that the super...

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Veröffentlicht in:Molecules (Basel, Switzerland) Switzerland), 2022-12, Vol.27 (24), p.8757
Hauptverfasser: Wang, Siqi, Zonov, Yaroslav V, Karpov, Victor M, Luzina, Olga A, Mezhenkova, Tatyana V
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Sprache:eng
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Zusammenfassung: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 FSO H-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 FSO H-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.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules27248757