Suzuki-Miyaura synthesis of m-terphenyl thioethers and their facilitated oxidation caused by through-space π···S···π interaction

S-tert-Butyl m-terphenyl thioethers have been efficiently synthesized by Suzuki-Miyaura coupling reactions with 2,6-dibromo-S-tert-butylthio benzene. Selective monocoupling could be achieved with o-substituted boronic acids. This facilitated the synthesis of unsymmetrical S-tert-butyl m-terphenyl thioethers and bis(S-tert-butyl m-terphenyl thioether)s. The study of their electrochemistry showed facilitated oxidations resulting from through-space π···S···π interactions.