Reduction of Aryl Thiocyanates with SmI(2) 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 SmI(2). 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 NO(2). The reactions may also be conducted with aryl bromides although with somewhat lower yields.
Still
Ian W. J.
IW
Department of Chemistry, Erindale College, University of Toronto, 3359 Mississauga Road North, Mississauga, Ontario, Canada L5L 1C6.
Toste
F. Dean
FD