Reduction of aryl thiocyanates with SmI2 and Pd-catalyzed coupling with aryl halides as a route to mixed aryl sulfides

A series of aryl iodides, with a range of substituents, has been successfully coupled using 10 mol % Pd catalyst with samarium thiolates, derived from the corresponding aryl thiocyanates upon reductive cleavage with SmI2. Reactions proceed in THF at 65 degrees C in yields ranging from good to excellent and are compatible with both electron-donating and electron-withdrawing substituents, except NO2. The reactions may also be conducted with aryl bromides although with somewhat lower yields.