Details

Autor(en) / Beteiligte

• Escopy, Samira
• Singh, Yashapal
• Demchenko, Alexei V

Titel

Palladium()-assisted activation of thioglycosides

Ist Teil von

• Organic & biomolecular chemistry, 2021-03, Vol.19 (9), p.244-254

Ort / Verlag

England: Royal Society of Chemistry

Erscheinungsjahr

2021

Link zum Volltext

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• Described herein is the first example of glycosidation of thioglycosides in the presence of palladium( ii ) bromide. While the activation with PdBr 2 alone was proven feasible, higher yields and cleaner reactions were achieved when these glycosylations were performed in the presence of propargyl bromide as an additive. Preliminary mechanistic studies suggest that propargyl bromide assists the reaction by creating an ionizing complex, which accelerates the leaving group departure. A variety of thioglycoside donors in reactions with different glycosyl acceptors were investigated to determine the initial scope of this new reaction. Selective and chemoselective activation of thioglycosides over other leaving groups has also been explored. Described herein is the first example of glycosidation of thioglycosides in the presence of palladium( ii ) bromide.