Sonogashira–Hagihara reactions of halogenated glycals

• Dennis C. Koester and
• Daniel B. Werz

Beilstein J. Org. Chem. 2012, 8, 675–682, doi:10.3762/bjoc.8.75

• glycals using several aromatic and aliphatic alkynes. This Pd-catalyzed cross-coupling reaction presents a facile access to alkynyl C-glycosides and sets the stage for a reductive/oxidative refunctionalization of the enyne moiety to regenerate either C-glycosidic structures or pyran derivatives with a

• substituent in position 2. Keywords: C-glycosides; enyne; glycals; reductive/oxidative refunctionalization; Sonogashira–Hagihara reaction; Introduction Carbohydrates are key players in a plethora of biological processes, such as cell-development, metastasis, cell–cell aggregation and viral infection [1][2