Room-Temperature Photochemical Copper-Mediated Fluorination of Aryl Iodides.

ABSTRACT

This report describes a method for the photochemical Cu-mediated fluorination of aryl iodides with AgF via putative aryl radical (Ar•) intermediates. It involves irradiating an aryl iodide with UVB light (λmax = 313 nm) in the presence of a mixture of CuI and CuII salts and AgF. Under these conditions, fluorination proceeds at room temperature for substrates containing diverse substituents, including alkoxy and alkyl groups, ketones, esters, sulfonate esters, sulfonamides, and protected amines. This method has been translated to radiofluorination using a combination of K18F, K3PO4, and AgOTf.