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

Nioch-logo

  

 старая версия сайта

 

Open Access

В журнале  Molecules (Издательство  MDPI, IF 4,2) по результатам работы, выполненной совместно с коллегой из Китая ( PetroChina Company Limited, Daqing)  опубликована статья, соавторами которой является сотрудники Института: к.х.н. Я.В. Зонов (снс, ЛГС),  аспирант В.В. Комаров (мнс, ЛГС), д.х.н. В.М. Карпов (гнс, ЛГС), к.х.н. Д.А. Пархоменко (снс, ЛМР) и д.х.н. Т.В. Меженкова (завлаб ЛГС) 

 

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

Yaroslav V. Zonov,  Siqi Wang,  Vladislav V. Komarov , Victor M. Karpov, Dmitriy A. Parkhomenko and Tatyana V. Mezhenkova

 

Molecules 2025, 30(4), 931;

Published: 17 February 2025

 

 DOI: 10.3390/molecules30040931

(This article belongs to the Section Organic Chemistry)

 

 

 

molecules-30-00931-ag-550

 

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.

 

Наука - навигация