Mild and Effective Method for the Nickel-Catalyzed Arylation of Glycosyl Thiols in Aqueous Surfactant Solution

Abstract

Aryl thioglycosides have broad applicability as both glycosyl donors and glycomimetic compounds. Their synthesis via the cross-coupling of glycosyl thiols with aryl halides has become a popular method for their construction because it allows better selectivity for anomeric configuration as well as a wider functional group tolerance compared to traditional methods. Herein, we report a nickel-catalyzed method for the synthesis of aryl thioglycosides which utilizes an aqueous micellar environment as the reaction medium. This alternative method allows for mild conditions while circumventing expensive palladium, leading to the successful synthesis of over 30 aryl thioglycosides, including challenging 1,2-cis thioglycoside products.