Microwave-assisted palladium-catalyzed cross-coupling reactions between pyranoid glycals and aryl bromides. Synthesis of 2′-deoxy C-aryl-β-glycopyranosides

Under microwave irradiation, perbenzylated pyranoid glycals were coupled with aryl bromides in the presence of 5% mol palladium(II) acetate in dimethylformamide to produce 2′,3′-unsaturated C-aryl-α-glycopyranosides in a rapid and stereospecific manner. The synthetic applicability of the method was further demonstrated by converting the resulting C-aryl glycosides to 2′-deoxy C-aryl-β-glycopyranosides through oxidation mediated by 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) and stereoselective reduction.