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Synthesis of S-Trifluoromethyl S-Arylsulfoximine Thioglycosides through Pd-Catalyzed Migita Cross-Coupling

  • Nedjwa Bennai
  • , Nada Ibrahim
  • , Jérôme Marrot
  • , Mohamed Belkadi
  • , Mouad Alami
  • , Emmanuel Magnier
  • , Elsa Anselmi
  • , Samir Messaoudi
  • Université Paris-Saclay
  • Université des Sciences et de Technologie d'Oran (USTO)
  • Faculté des Sciences et Techniques
  • Université de Tours

Research output: Contribution to journal › Article › peer-review

13 Citations (Scopus)

Abstract

A general protocol for the synthesis of S-trifluoromethyl S-arylsulfoximine thioglycosides has been reported. This protocol is based on a Pd-catalyzed Migita cross-coupling between o-iodo S-trifluoromethyl S-arylsulfoximines and a broad range of 1-thiosugars. This method gives access to a series of functionalized S-trifluoromethyl S-arylsulfoximine thioglycosides in moderate to good yields. Moreover, both diastereoisomers were easily separated by simple crystallization or by HPLC and full characterizations are provided for each pure trifluoromethylsulfoximine.

Original languageEnglish
Pages (from-to)4972-4981
Number of pages10
JournalEuropean Journal of Organic Chemistry
Volume2020
Issue number31
DOIs
Publication statusPublished - 23 Aug 2020
Externally publishedYes

Keywords

  • Cross-coupling
  • Glycosides
  • Homogeneous catalysis
  • Palladium
  • Synthetic methods

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