Visible-Light-Mediated Stadler–Ziegler Arylation of Thiosugars with Anilines

Abstract

Here, we report a one-pot Stadler−Ziegler reaction toward the synthesis of 1-thioglycosides in good yield from commercially available anilines and (un)protected 1-glycosyl thiols. This simple and mild approach employs the photoredox catalyst [Ru(bpy) 3 ](PF 6 ) 2 under visible light.

Recent Advances in Visible‐Light‐Driven C−S Bond Formation

“…Notably, both alkyl and aryl thiols were found suitable for the coupling. A protocol for the visible‐light mediated arylation of thiosugars with aryl diazonium salts generated in situ from the corresponding anilines was obtained via Stadler–Ziegler reaction was recently reported in literature [41] …”

Directed Dehydrogenative Copper‐Catalyzed C−H Thiolation in Pseudo‐Anomeric Position of Glycals using Thiol and Thiosugar Partners

“…Very recently, our group reported emergent and competitive activation processes toward thioglycosides such as photocatalysis [11] or electrocatalysis [12] (Scheme 1a). However, the use of non-activated partners faced with thiosugars via a CÀ H dehydrogenative cross-coupling pathway [13] is very scarce.…”

Advances in Organic and Inorganic Photoredox Catalysis

“…This protocol affords direct access to various S-aryl thioglycosides, which are valuable building synthons for drug discovery and chemical biology. 19 The visible-light photocatalytic functionalization of alkenes is a useful procedure for preparing high-value organic compounds. Zhu et al present an efficient method for synthesizing allylic and homoallylic azides through the visible-light-promoted photoredox-mediated difluoroalkylation of trisubstituted alkenes with ethyl bromodifluoroacetate.…”

“…Samir Messaoudi et al have developed a photoredox-catalyzed Stadler–Ziegler arylation of thiosugars with in situ -generated diazonium salts from anilines. This protocol affords direct access to various S -aryl thioglycosides, which are valuable building synthons for drug discovery and chemical biology …”

“…This protocol affords direct access to various S -aryl thioglycosides, which are valuable building synthons for drug discovery and chemical biology. 19 …”