Pd-catalyzed carbonylative cross-coupling reactions of 2-iodoglycals have been developed for the synthesis of sugar-based arylones and ynones using formic acid as the carbonyl source. Whereas acetyl-protected arylones lead to the formation of highly substituted furan derivatives in the presence of Lewis acid, benzyl-protected arylones furnished the 3-deoxy sugar derivative. In the presence of nucleophiles, an attack took place on the C-1 or C-3 carbon regio- and stereoselectively depending on the nature of the nucleophiles.