Radical reactions enabled by polyfluoroaryl fragments: photocatalysis and beyond

Zubkov, Mikhail O.; Dilman, Alexander D.

doi:10.1039/d3cs00889d

Chem. Soc. Rev.

2024

DOI: 10.1039/d3cs00889d

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Radical reactions enabled by polyfluoroaryl fragments: photocatalysis and beyond

Mikhail O. Zubkov,

Alexander D. Dilman

Abstract: The review summarizes advances in the radical chemistry of polyfluorinated arenes under photocatalytic conditions. The fluoroaryl fragment serves as enabling motif for the reaction design and efficient generation of reactive intermediates.

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Photocatalytic Functionalization of Alkenes Enabled by Polyfluoroaryl Migration

Savchenko,

Zubkov,

et al. 2024

ChemPhotoChem

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Visible light‐mediated photocatalytic approach for the radical functionalization of alkenes bearing the fluorinated aryl sulfide fragment is described. The process occurs in the presence of organic photocatalyst using sulfinates as sources of radicals. The key step of the reaction is the intramolecular 1,4‐migration of the polyfluoroaryl group. In the reaction, three new bonds are formed (two C‐C and one C‐S bond). The decisive role of fluorine atoms in the reaction efficiency was confirmed by DFT calculations.

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Photocatalytic Functionalization of Alkenes Enabled by Polyfluoroaryl Migration

Savchenko,

Zubkov,

et al. 2024

ChemPhotoChem

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Polyfluorinated benzoic acids as promising reagents for organic synthesis and medicinal chemistry

Shchegolkov,

Burgart,

Shchur

et al. 2024

RUSS CHEM REV

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Polyfluoroaromatic compounds occupy a special place in organic synthesis due to a wide range of their chemical transformations and unique biological properties. The introduction of the carboxyl function into polyfluoroarenes allows further diversification of the chemistry of these compounds. This review summarizes data on the chemical transformations of polyfluorobenzoic acids, including derivatives of polyfluorosalicylic acids. The reactions of esterification, amidation, reduction, decarboxylation, metal-catalyzed decarboxylative cross-coupling, C–H functionalization, reductive defluorination, nucleophilic aromatic substitution, heterocyclization and complex formation are considered. Reactivity features of polyfluorobenzoates in comparison to their non-fluorinated counterparts are highlighted. The potential for practical applications of polyfluorobenzoic acid derivatives, primarily as biologically active compounds, is presented. <br> Bibliography includes 300 references.

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Radical reactions enabled by polyfluoroaryl fragments: photocatalysis and beyond

Abstract: The review summarizes advances in the radical chemistry of polyfluorinated arenes under photocatalytic conditions. The fluoroaryl fragment serves as enabling motif for the reaction design and efficient generation of reactive intermediates.

Cited by 2 publications

References 250 publications

Photocatalytic Functionalization of Alkenes Enabled by Polyfluoroaryl Migration

Photocatalytic Functionalization of Alkenes Enabled by Polyfluoroaryl Migration

Polyfluorinated benzoic acids as promising reagents for organic synthesis and medicinal chemistry

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