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Carbonylation of Polyfluorinated 1-Arylalkan-1-ols and Diols in Superacids. / Wang, Siqi; Zonov, Yaroslav V; Karpov, Victor M et al.

In: Molecules (Basel, Switzerland), Vol. 27, No. 24, 10.12.2022, p. 8757.

Research output: Contribution to journalArticlepeer-review

Harvard

Wang, S, Zonov, YV, Karpov, VM, Luzina, OA & Mezhenkova, TV 2022, 'Carbonylation of Polyfluorinated 1-Arylalkan-1-ols and Diols in Superacids', Molecules (Basel, Switzerland), vol. 27, no. 24, pp. 8757. https://doi.org/10.3390/molecules27248757

APA

Wang, S., Zonov, Y. V., Karpov, V. M., Luzina, O. A., & Mezhenkova, T. V. (2022). Carbonylation of Polyfluorinated 1-Arylalkan-1-ols and Diols in Superacids. Molecules (Basel, Switzerland), 27(24), 8757. https://doi.org/10.3390/molecules27248757

Vancouver

Wang S, Zonov YV, Karpov VM, Luzina OA, Mezhenkova TV. Carbonylation of Polyfluorinated 1-Arylalkan-1-ols and Diols in Superacids. Molecules (Basel, Switzerland). 2022 Dec 10;27(24):8757. doi: 10.3390/molecules27248757

Author

Wang, Siqi ; Zonov, Yaroslav V ; Karpov, Victor M et al. / Carbonylation of Polyfluorinated 1-Arylalkan-1-ols and Diols in Superacids. In: Molecules (Basel, Switzerland). 2022 ; Vol. 27, No. 24. pp. 8757.

BibTeX

@article{84e30c7fff164d12a1ed2249159338dc,
title = "Carbonylation of Polyfluorinated 1-Arylalkan-1-ols and Diols in Superacids",
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.",
keywords = "Molecular Structure, Ethanol, Dicarboxylic Acids, Carbon Monoxide, carbonylation of alcohol, polyfluorinated compound, superacid, antimony pentafluoride, fluorosulfonic acid, trifluoromethanesulfonic acid",
author = "Siqi Wang and Zonov, {Yaroslav V} and Karpov, {Victor M} and Luzina, {Olga A} and Mezhenkova, {Tatyana V}",
note = "The authors are grateful to the Multi-Access Chemical Research Center of SB RAS for spectral and analytical measurements. Siqi Wang thanks the China Scholarship Council for its support.",
year = "2022",
month = dec,
day = "10",
doi = "10.3390/molecules27248757",
language = "English",
volume = "27",
pages = "8757",
journal = "Molecules",
issn = "1420-3049",
publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",
number = "24",

}

RIS

TY - JOUR

T1 - Carbonylation of Polyfluorinated 1-Arylalkan-1-ols and Diols in Superacids

AU - Wang, Siqi

AU - Zonov, Yaroslav V

AU - Karpov, Victor M

AU - Luzina, Olga A

AU - Mezhenkova, Tatyana V

N1 - The authors are grateful to the Multi-Access Chemical Research Center of SB RAS for spectral and analytical measurements. Siqi Wang thanks the China Scholarship Council for its support.

PY - 2022/12/10

Y1 - 2022/12/10

N2 - 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.

AB - 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.

KW - Molecular Structure

KW - Ethanol

KW - Dicarboxylic Acids

KW - Carbon Monoxide

KW - carbonylation of alcohol

KW - polyfluorinated compound

KW - superacid

KW - antimony pentafluoride

KW - fluorosulfonic acid

KW - trifluoromethanesulfonic acid

UR - https://www.scopus.com/record/display.uri?eid=2-s2.0-85144555755&origin=inward&txGid=b93ad76738ab588323fc80ada5da449a

UR - https://www.mendeley.com/catalogue/26f142bd-21b0-33a2-9c79-f3a0992f77ca/

U2 - 10.3390/molecules27248757

DO - 10.3390/molecules27248757

M3 - Article

C2 - 36557890

VL - 27

SP - 8757

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 24

ER -

ID: 42568334