Chalcogenylation of Naphthalene Derivatives Catalyzed by Iron(III) Chloride and Potassium Iodide

We have developed an efficient chalcogenylation of electron-rich naphthalene derivatives catalyzed by FeCl3 and KI. The methodology provides access to several nonsymmetrical diorganoyl chalcogenides (S, Se) by selective C1 chalcogenylation of 2-naphthols or 2-naphthylamines using simple and cheap catalysts. Several control experiments supported the hypothesis that a redox reaction between Fe(III) and KI produces I2, which catalyzed the chalcogenylation.