Regio- and stereo-selective synthesis of aryl 2-deoxy-C-glycopyranosides by palladium-catalyzed Heck coupling reactions of glycals and aryl iodides

The Heck coupling of aryl iodides with pyranoid glycals using a catalytic amount of Pd(OAc)(2) to form pyranoid aryl C-glycosides has been achieved. The reaction takes place smoothly in the presence of Ag2CO3 and Cu(OAc)(2) (or DMSO) in acetonitrile. This arylation process, which occurs in a highly regio- and stereo-selective manner, provides a simple, mild, and efficient approach to the synthesis of aryl 2-deoxy-C-glycopyranosides.