Palladium-Catalyzed Cross-Couplings of Aryl Thianthrenium Salts with N-Tosylhydrazones for the Synthesis of 1,1-Diarylalkenes

An efficient palladium-catalyzed cross-coupling of aryl thianthrenium salts with N-tosylhydrazones has been successfully developed, enabling the facile construction of a diverse array of valuable 1,1-diarylalkenes. The reactions proceeded well through C–S bond cleavage in the presence of Pd(OAc)2 as a catalyst, Xphos as a ligand, and LiOtBu as a base, showing both good substrate scope and wide functional group compatibility. Additionally, applications of the method in the late-stage diversification of bioactive complex molecules and gram-scale synthesis could be accomplished as well. Noteworthily, the one-pot, two-step reactions directly commencing from the utilization of arenes as starting materials with the aid of thianthrene S-oxide (TTSO) and Tf2O to in situ transform arenes into aryl thianthrenium salts followed by subsequent palladium-catalyzed couplings with N-tosylhydrazones could also be realized.