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Abstract | Cited by

Copper-mediated couplings of arylboroxines with glycosyl hemiacetals furnish O-aryl glycosides via Csp2–O bond formation. The method enables the anomeric O-arylation of protected pyranose and furanose derivatives, and is tolerant of functionalized arylboroxine partners. Whereas mixtures of anomers are formed from glucopyranose, galactopyranose and arabinofuranose hemiacetals, the α-anomer is generated selectively from mannopyranose and mannofuranose-derived substrates.

Graphical abstract: Copper-mediated anomeric O-arylation with organoboron reagents

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