Palladium catalyzed stereocontrolled synthesis of C-aryl glycosides using glycals and arenediazonium salts at room temperatureDedicated to Professor Peter H. Seeberger on the occasion of his 50th birthday.Electronic supplementary information (ESI) available: Experimental procedures and copies of 1H NMR and 13C NMR spectra of 1aa-1aj, 3aa-3ce, 4ab, mixture of 3ab + 5ab, 4ba, 4bf, and 5ba. See DOI: 10.1039/c8ob01393d

A stereocontrolled synthesis of aryl- C -glycosides was achieved using glycals and aryldiazonium salts in the presence of palladium acetate. A wide range of glycals including d -glucal, d -galactal, l -rhamnal, d -xylal and d -ribal underwent C -arylation at the anomeric carbon in the presence of different aryldiazonium tetrafluoroborates and gave synthetically useful 2,3-deoxy-3-keto-α-aryl- C -glycosides in good to excellent yields. Broad substrate scope, simple operation and room temperature reactions make this protocol very attractive in organic synthesis. A wide range of glycals underwent C -arylation with aryldiazonium tetrafluoroborates and provided synthetically useful 2,3-deoxy 3-keto α-aryl- C -glycosides in good to excellent yields.