4.6 Article

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

Journal

MOLECULES
Volume 27, Issue 24, Pages -

Publisher

MDPI
DOI: 10.3390/molecules27248757

Keywords

carbonylation of alcohol; superacid; polyfluorinated compound; fluorosulfonic acid; trifluoromethanesulfonic acid; antimony pentafluoride

Ask authors/readers for more resources

This study describes the carbonylation reactions of mono and dihydroxy derivatives of polyfluorinated alkylbenzenes and benzocycloalkenes with benzylic hydroxyl groups in the presence of a superacid. The efficiency of different superacids was evaluated, and FSO3H-SbF5 showed the best results in most transformations.
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 alpha,beta-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.

Authors

I am an author on this paper
Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.6
Not enough ratings

Secondary Ratings

Novelty
-
Significance
-
Scientific rigor
-
Rate this paper

Recommended

No Data Available
No Data Available