Photoredox-Catalyzed Synthesis of <i>C</i>-Benzoselenazolyl/Benzothiazolyl Glycosides from 2-Isocyanoaryl Selenoethers/Thioethers and Glycosyl Bromides
Yi Jiao, Xiaoran Shi, Lei Ju, Shouyun Yu
Abstract
Molecules containing heteroatoms, such as Se and S, play an indispensable role in the discovery and design of pharmaceuticals, whereas Se has been less studied. Here, we described a photoredox strategy to synthesize C -benzoselenazolyl (Bs) glycosides from 2-isocyanoaryl selenoethers and glycosyl bromides. This reaction was carried out under mild conditions with high efficiency. C -Benzothiazolyl (Bt) glycosides could also be synthesized from 2-isocyanoaryl thioethers using this strategy. This method can access novel seleno/thiosugars, which will benefit Se/S-containing drug discovery.
Topics & Concepts
ChemistryGlycosylGlycosideCatalysisOrganic chemistryCombinatorial chemistryStereochemistryMedicinal chemistrySulfur-Based Synthesis TechniquesRadical Photochemical ReactionsFluorine in Organic Chemistry