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

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

Журнал

Molecules
, E-ISSN: 1420-3049

Вых. Данные

Год: 2025, Том: 30, Номер: 4, Номер статьи : 931, Страниц : DOI: 10.3390/molecules30040931

Ключевые слова

carbonylation; carbon monoxide; benzyl chloride; benzyl fluoride; polyfluorinated compound; carboxylic acid; antimony pentafluoride

Авторы

Zonov Yaroslav V. ^1,2 , Wang Siqi ³ , Komarov Vladislav V. ¹ , Karpov Victor M. ¹ , Parkhomenko Dmitriy A. ¹ , Mezhenkova Tatyana V. ¹

Организации

1	N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS
2	Department of Natural Sciences, Novosibirsk State University
3	Daqing Petrochemical Research Center, PetroChina Company Limited

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.

Zonov Y.V. , Wang S. , Komarov V.V. , Karpov V.M. , Parkhomenko D.A. , Mezhenkova T.V.
Carbonylation of Polyfluorinated Alkylbenzenes and Benzocycloalkenes at the Benzyl C-F and C-Cl Bonds Under the Action of CO/SbF5
Molecules. 2025. V.30. N4. 931 . DOI: 10.3390/molecules30040931 WOS OpenAlex

Поступила в редакцию:	17 янв. 2025 г.
Принята к публикации:	14 февр. 2025 г.
Опубликована в печати:	17 февр. 2025 г.
Опубликована online:	17 февр. 2025 г.

Web of science:	WOS:001431918000001
OpenAlex:	W4407640324

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