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Electrochemically Mediated S-Glycosylation of 1-Thiosugars with Xanthene Derivatives.

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An efficient electrochemical dehydrogenative cross-coupling of benzylic C-H bonds with 1-thiosugars at room temperature is described. The direct S-glycosylation protocol avoids using any oxidant, which provides facile access to various… Click to show full abstract

An efficient electrochemical dehydrogenative cross-coupling of benzylic C-H bonds with 1-thiosugars at room temperature is described. The direct S-glycosylation protocol avoids using any oxidant, which provides facile access to various glycosylated xanthene derivatives with up to 91% yield. This current electrooxidative reaction is characterized by high atom economy, high efficiency, mild reaction conditions, being environmentally benign, and excellent functional group tolerance. Moreover, preliminary mechanistic investigations reveal that the reaction involves a free radical process.

Keywords: electrochemically mediated; thiosugars xanthene; glycosylation; mediated glycosylation; glycosylation thiosugars; xanthene derivatives

Journal Title: Organic letters
Year Published: 2023

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