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

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Pd-Catalyzed Alkenyl Thioether Synthesis from Thioesters and N-Tosylhydrazones
Ishitobi, K.; Muto, K.; Yamaguchi, J.
ACS Catal. 2019, ASAP.
DOI: 10.1021/acscatal.9b04212

 A Pd-catalyzed alkenyl thioether synthesis was achieved using thioesters and N -tosylhydrazones as startingmaterials. 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.

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