Stereoretentive Copper‐Catalyzed Directed Thioglycosylation of C(sp2)−H Bonds of Benzamides. Issue 42 (25th August 2016)

• Record Type: Journal Article
• Authors: Chabrier, Amélie; Bruneau, Alexandre; Benmahdjoub, Sara; Benmerad, Belkacem; Belaid, Sabrina; Brion, Jean‐Daniel; Alami, Mouâd; Messaoudi, Samir
• Is Part Of: Chemistry. Volume 22:Issue 42(2016)
• Page Start: 15006
• Page End: 15010
• Publication Date: 2016-08-25
• Subjects: C−H bond activation -- copper -- homogeneous catalysis -- thioglycosides -- thioglycosylation reaction; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201602909
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: An efficient thioglycosylation of C(sp 2 )−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. Abstract : Pour some thiosugar on CH : An efficient thioglycosylation of C(sp 2 )−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 (see scheme).