This method demonstrates β-selective glycosylation of glucals with aryl iodides, suggesting enhanced efficiency. It employs a nickel catalyst and pentafluorobenzoate as a leaving group.
Inspired by the excellent stereoinduction of palladium catalytic glycosylation with glycals via an inner-sphere pathway, a nickel-catalyzed, stereoselective C-aryl glycosylation has been developed for glucals bearing a pentafluorobenzoate (PFB) group at the C3 position. The extremely electron-deficient nature of PFB not only endows stronger activity compared to the traditional leaving groups but also functions as an orientation group, presumably through the strong π-π interactions with the bipyridine ligand coordinated to the nickel center, thereby enabling the β-selective formation of a C-aryl glycosidic bond with aryl iodides as glycosyl acceptors under mild conditions. This method features a broad substrate scope, high efficiency, and scalability, providing a general solution to the synthesis of challenging β-C-glycosides.
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Wu et al. (2025) studied this question.
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