Palladium-catalyzed cross-coupling via the C(sp(2))-S bond activation of aryl thioethers and the C-H bond activation of azoles or thiazoles was carried out. Electron-deficient and -rich aryl methyl thioethers and diaryl thioethers can be employed as the coupling partners and the reaction tolerates a range of functional groups including MeO, CF3, CN, PhCO, CONEt2, and Py groups.