PubAg

Main content area

Decarboxylative Fluorination of Aliphatic Carboxylic Acids via Photoredox Catalysis

Author:
Ventre, Sandrine, Petronijevic, Filip R., MacMillan, David W. C.
Source:
Journal of the American Chemical Society 2015 v.137 no.17 pp. 5654-5657
ISSN:
1520-5126
Subject:
carboxylic acids, catalytic activity, fluorides, free radicals, oxidation, standard operating procedures
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.
Agid:
5410020