A broader generality of the disclosed protocol was investigated with a series of glycosides and somophile coupling partners (Fig. ). Several β-glycosides bearing sensitive aglycones successfully engaged in the reaction with methyl acrylate somophile (Fig. ). A common para-methoxyphenyl anomeric protecting group did not impede formation of the expected product (3f, 62% yield), despite being sensitive to both oxidative and acidic conditions. Furthermore, employing βGlc 1→6 αGal partially-protected disaccharide as the substrate delivered the desired C4-functionalized product 3g in 40% yield, which could present a significant regioselectivity challenge for the alternative C-H functionalization strategies proceeding through intermolecular HAT. A substrate derived from the common visualization agent X-Gal, bearing polyfunctionalized 5-bromo-4-chloro-3-indolyl aglycone, produced the expected product 3h in a reasonable yield of 39%, despite being designed to undergo facile glycosidic bond cleavage to release the corresponding indigo dye derivative. Finally, employing a naturally-occurring phenolic glycoside curculigoside G 53 as the substrate produced the C4-functionalized product 3i, albeit in lower yield (26%), despite bearing oxidatively-sensitive aglycone with multiple sites for potential deleterious HAT reactions.