Oxidant-controlled heck-type C-glycosylation of glycals with arylboronic acids: stereoselective synthesis of aryl 2-deoxy-C-glycosides.Org Lett. 2009 Apr 16; 11(8):1709-12.OL
Oxidative Heck-type C-glycosylations of glycals with various arylboronic acids using Pd(OAc)(2) as catalyst in the presence of oxidant were developed. The corresponding ketone, enol ether, and enone types of C-glycosides were predictably obtained with benzoquinone (BQ), Cu(OAc)(2)/O(2), and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as oxidants, respectively. This method provides a simple, mild, and stereoselective synthesis of aryl 2-deoxy-C-glycosides.