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Decarboxylative Fluorination of Aliphatic Carboxylic Acids via Photoredox Catalysis.

ABSTRACT: The direct conversion of aliphatic carboxylic acids to the corresponding alkyl fluorides has been achieved via visible light-promoted photoredox catalysis. This operationally simple, redox-neutral fluorination method is amenable to a wide variety of carboxylic acids. Photon-induced oxidation of carboxylates leads to the formation of carboxyl radicals, which upon rapid CO2-extrusion and F(•) transfer from a fluorinating reagent yield the desired fluoroalkanes with high efficiency. Experimental evidence indicates that an oxidative quenching pathway is operable in this broadly applicable fluorination protocol.

SUBMITTER: Ventre S

PROVIDER: S-EPMC4862610 | biostudies-literature | 2015 May

REPOSITORIES: biostudies-literature

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Decarboxylative Fluorination of Aliphatic Carboxylic Acids via Photoredox Catalysis.

Ventre Sandrine S Petronijevic Filip R FR MacMillan David W C DW

Journal of the American Chemical Society 20150427 17

The direct conversion of aliphatic carboxylic acids to the corresponding alkyl fluorides has been achieved via visible light-promoted photoredox catalysis. This operationally simple, redox-neutral fluorination method is amenable to a wide variety of carboxylic acids. Photon-induced oxidation of carboxylates leads to the formation of carboxyl radicals, which upon rapid CO2-extrusion and F(•) transfer from a fluorinating reagent yield the desired fluoroalkanes with high efficiency. Experimental ev ...[more]

PMID: 25881929

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