Rapid and scalable synthesis of fluoroketones via cerium-mediated C–C bond cleavage

Abstract

Ketones with remote fluorination are an important motif in the synthesis of bioactive molecules. Here we demonstrate that ceric ammonium nitrate (CAN) is able to produce this functionality under incredibly mild conditions and short reaction times (30 min) while eliminating the need for precious metals in previous methods. Importantly, this method allows the efficient synthesis of a wide variety of γ-fluoroketones and is highly scalable. Preliminary mechanistic studies suggest this reaction proceeds through a radical pathway.