Convenient synthesis of pentafluoroethyl thioethers via catalytic Sandmeyer reaction with a stable fluoroalkylthiolation reagent

Abstract

Aromatic and heteroaromatic diazonium salts were smoothly converted into the corresponding pentafluoroethyl thioethers by reaction with Me₄NSC₂F₅ in the presence of catalytic amounts of elemental copper. This Sandmeyer-type reaction proceeds at room temperature under mild conditions and is applicable to a wide range of functionalised molecules. It enables the late-stage introduction of pentafluoroethylthio groups, a promising but largely unexplored substituent, into bioactive molecules.