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–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.

Cite: Wang S. , Zonov Y.V. , Karpov V.M. , Luzina O.A. , Mezhenkova T.V.
Carbonylation of Polyfluorinated 1-Arylalkan-1-ols and Diols in Superacids
Molecules. 2022. V.27. N24. P.8757. DOI: 10.3390/molecules27248757 WOS РИНЦ

Dates:

Submitted:	Nov 19, 2022
Accepted:	Dec 8, 2022
Published online:	Dec 10, 2022

Identifiers:

Web of science	WOS:000902954000001
Elibrary	58858452
OpenAlex	W4312126372

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