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

Siqi Wang, Yaroslav V Zonov, Victor M Karpov, Olga A Luzina, Tatyana V Mezhenkova

Результат исследования: Научные публикации в периодических изданияхстатьярецензирование


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-SbF5 mixture, or a FSO3H-SbF5 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 FSO3H-SbF5 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 α,β-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.

Язык оригиналаанглийский
Страницы (с-по)8757
ЖурналMolecules (Basel, Switzerland)
Номер выпуска24
СостояниеОпубликовано - 10 дек. 2022

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