Standard

Carbonylation of Polyfluorinated Alkylbenzenes and Benzocycloalkenes at the Benzyl C-F and C-Cl Bonds Under the Action of CO/SbF5. / Zonov, Yaroslav V.; Wang, Siqi; Komarov, Vladislav V. et al.

In: Molecules, Vol. 30, No. 4, 931, 17.02.2025.

Research output: Contribution to journal › Article › peer-review

Harvard

Zonov, YV, Wang, S, Komarov, VV, Karpov, VM, Parkhomenko, DA & Mezhenkova, TV 2025, 'Carbonylation of Polyfluorinated Alkylbenzenes and Benzocycloalkenes at the Benzyl C-F and C-Cl Bonds Under the Action of CO/SbF5', Molecules, vol. 30, no. 4, 931. https://doi.org/10.3390/molecules30040931

APA

Zonov, Y. V., Wang, S., Komarov, V. V., Karpov, V. M., Parkhomenko, D. A., & Mezhenkova, T. V. (2025). Carbonylation of Polyfluorinated Alkylbenzenes and Benzocycloalkenes at the Benzyl C-F and C-Cl Bonds Under the Action of CO/SbF5. Molecules, 30(4), [931]. https://doi.org/10.3390/molecules30040931

Vancouver

Zonov YV, Wang S, Komarov VV, Karpov VM, Parkhomenko DA, Mezhenkova TV. Carbonylation of Polyfluorinated Alkylbenzenes and Benzocycloalkenes at the Benzyl C-F and C-Cl Bonds Under the Action of CO/SbF5. Molecules. 2025 Feb 17;30(4):931. doi: 10.3390/molecules30040931

Author

Zonov, Yaroslav V. ; Wang, Siqi ; Komarov, Vladislav V. et al. / Carbonylation of Polyfluorinated Alkylbenzenes and Benzocycloalkenes at the Benzyl C-F and C-Cl Bonds Under the Action of CO/SbF5. In: Molecules. 2025 ; Vol. 30, No. 4.

BibTeX

@article{49ca06c1be434e469eab8eb8a6acc662,
title = "Carbonylation of Polyfluorinated Alkylbenzenes and Benzocycloalkenes at the Benzyl C-F and C-Cl Bonds Under the Action of CO/SbF5",
abstract = "The carbonylation at the benzyl C-Hal bonds (Hal = F, Cl) of a number of polyfluorinated alkylbenzenes and benzocycloalkenes using carbon monoxide in the presence of SbF5 is described. The reaction provided the corresponding α-arylcarboxylic acids or their methyl esters following aqueous or methanol treatment. The products of double carbonylation were obtained from bis(chloromethyl)tetrafluorobenzenes and benzal fluorides. For benzal chloride derivatives, the possibility of selective mono- or dicarbonylation was shown to depend on the amount of antimony pentafluoride. In the case of polyfluorinated secondary benzyl halides with a hydrogen atom at the α-carbon atom and vicinal fluorine atoms, the addition of CO was found to be accompanied by the elimination of HF, resulting in α,β-unsaturated α-arylcarboxylic acids. The double elimination of HF during the carbonylation of 1,4-dichloro-2,2,3,3,5,6,7,8-octafluorotetralin yielded dimethyl perfluoronaphthalene-1,4-dicarboxylate.",
keywords = "antimony pentafluoride, benzyl chloride, benzyl fluoride, carbon monoxide, carbonylation, carboxylic acid, polyfluorinated compound",
author = "Zonov, {Yaroslav V.} and Siqi Wang and Komarov, {Vladislav V.} and Karpov, {Victor M.} and Parkhomenko, {Dmitriy A.} and Mezhenkova, {Tatyana V.}",
year = "2025",
month = feb,
day = "17",
doi = "10.3390/molecules30040931",
language = "English",
volume = "30",
journal = "Molecules",
issn = "1420-3049",
publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",
number = "4",

}

RIS

TY - JOUR

T1 - Carbonylation of Polyfluorinated Alkylbenzenes and Benzocycloalkenes at the Benzyl C-F and C-Cl Bonds Under the Action of CO/SbF5

AU - Zonov, Yaroslav V.

AU - Wang, Siqi

AU - Komarov, Vladislav V.

AU - Karpov, Victor M.

AU - Parkhomenko, Dmitriy A.

AU - Mezhenkova, Tatyana V.

PY - 2025/2/17

Y1 - 2025/2/17

N2 - The carbonylation at the benzyl C-Hal bonds (Hal = F, Cl) of a number of polyfluorinated alkylbenzenes and benzocycloalkenes using carbon monoxide in the presence of SbF5 is described. The reaction provided the corresponding α-arylcarboxylic acids or their methyl esters following aqueous or methanol treatment. The products of double carbonylation were obtained from bis(chloromethyl)tetrafluorobenzenes and benzal fluorides. For benzal chloride derivatives, the possibility of selective mono- or dicarbonylation was shown to depend on the amount of antimony pentafluoride. In the case of polyfluorinated secondary benzyl halides with a hydrogen atom at the α-carbon atom and vicinal fluorine atoms, the addition of CO was found to be accompanied by the elimination of HF, resulting in α,β-unsaturated α-arylcarboxylic acids. The double elimination of HF during the carbonylation of 1,4-dichloro-2,2,3,3,5,6,7,8-octafluorotetralin yielded dimethyl perfluoronaphthalene-1,4-dicarboxylate.

AB - The carbonylation at the benzyl C-Hal bonds (Hal = F, Cl) of a number of polyfluorinated alkylbenzenes and benzocycloalkenes using carbon monoxide in the presence of SbF5 is described. The reaction provided the corresponding α-arylcarboxylic acids or their methyl esters following aqueous or methanol treatment. The products of double carbonylation were obtained from bis(chloromethyl)tetrafluorobenzenes and benzal fluorides. For benzal chloride derivatives, the possibility of selective mono- or dicarbonylation was shown to depend on the amount of antimony pentafluoride. In the case of polyfluorinated secondary benzyl halides with a hydrogen atom at the α-carbon atom and vicinal fluorine atoms, the addition of CO was found to be accompanied by the elimination of HF, resulting in α,β-unsaturated α-arylcarboxylic acids. The double elimination of HF during the carbonylation of 1,4-dichloro-2,2,3,3,5,6,7,8-octafluorotetralin yielded dimethyl perfluoronaphthalene-1,4-dicarboxylate.

KW - antimony pentafluoride

KW - benzyl chloride

KW - benzyl fluoride

KW - carbon monoxide

KW - carbonylation

KW - carboxylic acid

KW - polyfluorinated compound

UR - https://www.mendeley.com/catalogue/8c497279-fcd3-3316-a247-ade1be233e06/

UR - https://www.scopus.com/record/display.uri?eid=2-s2.0-85219195143&origin=inward&txGid=18d97778b42f3e832f198a22c6cd1f1c

UR - https://pubmed.ncbi.nlm.nih.gov/40005241/

UR - https://pmc.ncbi.nlm.nih.gov/articles/PMC11858302/

U2 - 10.3390/molecules30040931

DO - 10.3390/molecules30040931

M3 - Article

C2 - 40005241

VL - 30

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 4

M1 - 931

ER -

ID: 64945915