title: 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.
authors.affiliation: Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544, United States.
authors.forename: Sandrine
authors.initials: S
authors.lastname: Ventre
authors.affiliation: Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544, United States.
authors.forename: Filip R
authors.initials: FR
authors.lastname: Petronijevic
authors.affiliation: Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544, United States.
authors.forename: David W C
authors.initials: DW
authors.lastname: MacMillan
mesh_terms: D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D003653:Decarboxylation; D054879:Halogenation; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D055668:Photochemical Processes
chemical_list: D002264:Carboxylic Acids; D006845:Hydrocarbons, Fluorinated