Photocatalytic hydroperfluoroalkylation of alkenes was developed at the ZIOC

Organofluorine compounds are actively used in modern science and technology. Among them are medicines, refrigerants, pesticides. One of the most important methods for the synthesis of organofluorine compounds is the addition of fluorine-containing radical species to multiple bonds. The electron-withdrawing effect of fluorine promotes one-electron reduction of fluorinated alkyl halides, leading to the formation of alkyl radicals. Fluorinated iodides and bromides are most often used in such processes. The latter are more accessible, but much less reactive.

A method for photocatalytic hydroperfluoroalkylation of alkenes has been developed at the Laboratory of Functional Organic Compounds of the Zelinsky Institute. The available freon 1,2-dibromotetrafluoroethane was used as a fluorinating agent. The reaction proceeds under mild conditions when irradiated with blue light in the presence of a photocatalyst that does not contain heavy metal atoms. Inexpensive and available ascorbic acid was used as a reducing agent. In the course of the study, it was also shown that the obtained tetrafluorobromides can be successfully used for the synthesis of a wide range of organofluorine compounds by functionalization of the carbon-bromine bond.

Source:

Vladislav S. Kostromitin, Vitalij V. Levin, and Alexander D. Dilman Organophotoredox-Catalyzed Reductive Tetrafluoroalkylation of Alkenes J. Org. Chem. 2022, accepted manuscript. DOI: 10.1021/acs.joc.2c00712.