Simple preparation of phenylpropenoid β-d-glucopyranoside congeners by Mizoroki–Heck type reaction using organoboron reagents

Palladium(II)-catalyzed carbon–carbon bond formation between allyl 2,3,4,6-tetra-O-acetyl-β-d-glucopyranoside () and arylboronic acid congeners gave the corresponding cinnamyl 2,3,4,6-tetra-O-acetyl- β-d-glucopyranosides () in good yield. Among them, coupling products were converted to not only the naturally occurring phenylpropenoid β-d-glucopyranoside analogues () but also the unnaturally ones ().