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Reaction of Perfluoroalkyl Grignard Reagents with Phosphorus Trihalides: A New Route to Perfluoroalkyl-phosphonous and -phosphonic Acids

Our investigation shows that the previously unreported reaction of perfluoroalkyl Grignards with phosphorus (III) halides results in selective mono-substitution. Hydrolytic work-up gives (perfluoroalkyl)phosphonous acids, and subsequent oxidation cleanly produces (perfluoroalkyl)phosphonic acids. The many patented applications of these acids include as antifoaming agents, as ligand components for optical gain media, as lubricants for micro/nano-optical mechanical systems and as fluorinated ion-exchange membranes in fuel cells. Nevertheless, developments of these applications had previously been hindered due to the difficulties in synthesizing these compounds. The convenient high yield, atom-efficient, one pot synthesis developed in our paper is thus a significant contribution to the area.