Modular Synthesis of Aryl Thio/Selenoglycosides via the Catellani Strategy
Yanan Ding, Yan‐Chong Huang, Wei‐Yu Shi, Nian Zheng, Cui‐Tian Wang, Xi Chen, Yang An, Zhe Zhang, Yong‐Min Liang
Abstract
We described a novel palladium-catalyzed domino procedure for the preparation of (hetero)aryl thio/selenoglycosides. Readily available (hetero)aryl iodides and easily accessible 1-thiosugars/1-selenosugars are utilized as the substrates. Meanwhile, 10 types of sugars are quite compatible with this reaction with good regio- and stereoselectivity, high efficiency, and broad applicability (up to 89%, 53 examples). This method enables the straightforward formation of the C(sp2)–S/Se bond of (hetero)aryl thio/selenoglycosides.
Topics & Concepts
Thio-ArylChemistryStereoselectivityDominoCombinatorial chemistryPalladiumModular designCatalysisStereochemistryOrganic chemistryComputer scienceProgramming languageAlkylCarbohydrate Chemistry and SynthesisSulfur-Based Synthesis TechniquesChemical Synthesis and Reactions