Stereoretentive Copper-Catalyzed Directed Thioglycosylation of C(sp2 )-H Bonds of Benzamides

Chemistry. 2016 Oct 10;22(42):15006-15010. doi: 10.1002/chem.201602909. Epub 2016 Aug 25.

Abstract

An efficient thioglycosylation of C(sp2 )-H bonds with thiosugars has been established for the first time. Using only Cu(OAc)2 ⋅H2 O as a catalyst and Ag2 CO3 as an additive in DMSO, the protocol proved to have broad scope, and a variety of complex thioglycosides have been prepared in good yields with exclusive β-selectivity.

Keywords: C−H bond activation; copper; homogeneous catalysis; thioglycosides; thioglycosylation reaction.