Photoinduced copper-catalyzed alkoxycarbonylation of alkyl fluorides

Abstract

As the strongest σ bond in organic chemistry, the functionalization of the carbon-fluoride bond (BDE = 485 kJ mol−1) remains a significant challenge. Herein, we developed a carbonylation procedure that utilizes a copper catalyst and visible light irradiation to enable the production of esters from alkyl fluorides and phenols for the first time. From our mechanistic studies, the use of magnesium iodide as an additive was found to be crucial for the success of this protocol which drives the halide exchange and removes fluoride from the reaction.