Pd-Catalyzed Alkenyl Thioether Synthesis from Thioesters and N-Tosylhydrazones

Article abstract of DOI:10.1021/acscatal.9b04212

A Pd-catalyzed alkenyl thioether synthesis was achieved using thioesters and N-tosylhydrazones as starting materials. The thioester acted as an efficient "sulfur source" for catalytic C-S bond formation using N-tosylhydrazone. This method gave Z-alkenyl thioethers with high diastereoselectivity (up to 99:1 diastereomeric ratio). This transformation displayed a wide functional group tolerance and was successfully applied to the late-stage derivatization of a pharmaceutical molecule to the corresponding alkenyl thioether.