Synthesis of S-acetyl oligoarylenedithiols via Suzuki-Miyaura cross-coupling

Oligoarylenes with three or four aromatic rings, bearing two S-acetylated mercaptomethyl groups in 1,3 position on one end of the polyaromatic system and presenting various functionalities on the other terminal ring, have been synthesized by the Suzuki-Miyaura cross-coupling reaction. The use of palladium complexes with a Buchwald's phosphine as ligand allowed us to perform this coupling reaction also in the presence of benzylic S-acetyl-protected functionalities on the aromatic halide. The obtained oligoarylenes are potential novel candidates for the generation of self-assembling monolayers on metal substrates.