Work

Decarboxylative Fluorination of Aliphatic Carboxylic Acids via Photoredox Catalysis

Year: 2015

Type: article

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.

Source: Journal of the American Chemical Society

DOI: 10.1021/jacs.5b02244

Authors: Sandrine Ventre, Filip R. Petronijevic, David W. C. MacMillan

Institution: Princeton University

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Amgen, Merck, AbbVie, National Institute of General Medical Sciences

Award: New Strategies in Metallaphotoredox Catalysis