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

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Abstract

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.

Original languageEnglish
Pages (from-to)11685-11690
Number of pages6
JournalACS Catalysis
Volume9
Issue number12
DOIs
Publication statusPublished - 2019 Dec 6

Keywords

  • catalytic reaction
  • N-tosylhydrazone
  • Pd-carbene
  • thioester
  • thioether

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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