DOI: 10.1021/acs.orglett.6c03933 ISSN: 1523-7060
Photocatalytic Three-Component Glycosylation of Styrenes with Glycosyl Acids and Pyridines via Decarboxylation
Jingyi Guo, Xin Liu, Jin Yang, Jingyu Zhang, Yingsheng ZhaoAbstract
C-Alkyl glycosides represent important pharmaceutical scaffolds; however, most methods require two-component reactions. We report a visible-light-mediated three-component tandem decarboxylative difunctionalization of glycosyl acids, styrenes, and cyanopyridines for one-step assembly of polysubstituted C-glycosides. The method tolerates various styrenes, protected monosaccharides, and pharmaceutically active fragments, and enables gram-scale preparation. Mechanistic studies confirm a glycosyl-radical tandem pathway. This study addresses a key gap in styrene-participating multicomponent sugar reactions, providing a concise strategy for C-glycoside synthesis.