Palladium-Catalyzed Thiocarbonylations with Triisopropylsilyl Thioethers

Yosuke Hosoya, Kota Mizoguchi, Honoka Yasukochi, Masahisa Nakada*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

We have developed a palladium-catalyzed thiocarbonylation through the reaction of a σ-alkyl palladium intermediate with carbon monoxide and a triisopropylsilyl (TIPS) thioether. The use of CsF, (IPr)Pd(allyl)Cl [IPr =1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene], CO, and a TIPS thioether in THF are key to obtaining alkyl and aryl thioesters in high yields. The yield of the palladium-catalyzed thiocarbonylation depended on the structure of the substrate; indoline-2-one derivatives were formed faster than indoline derivatives. The reactions of benzoyl and hydrocinnamoyl fluorides with TIPSSPh and CsF also gave the corresponding thioesters.

Original languageEnglish
Pages (from-to)495-501
Number of pages7
JournalSynlett
Volume33
Issue number5
DOIs
Publication statusPublished - 2022 Mar 17

Keywords

  • acyl fluorides
  • palladium catalysis
  • thiocarbonylation
  • thioesters
  • thioethers

ASJC Scopus subject areas

  • Organic Chemistry

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