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 (1) , Elsa Anselmi , Samir Messaoudi

1 CNRS - Centre National de la Recherche Scientifique

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.

Domaines: Chimie organique

Nedjwa Bennai, Nada Ibrahim, Jérôme Marrot, Mohamed Belkadi, Mouad Alami, et al.. Synthesis of S-Trifluoromethyl S-Arylsulfoximine Thioglycosides through Pd-Catalyzed Migita Cross-Coupling. European Journal of Organic Chemistry, 2020, ⟨10.1002/ejoc.202000821⟩. ⟨hal-02992809⟩