Modular Synthesis of Aryl Thio/Selenoglycosides via the Catellani Strategy

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(sp(2))-S/Se bond of (hetero)aryl thio/selenoglycosides.

Automated summary

A novel palladium-catalyzed domino procedure has been described for the preparation of (hetero)aryl thio/selenoglycosides, utilizing readily available (hetero)aryl iodides and easily accessible 1-thiosugars/1-selenosugars as substrates. The method shows good regio- and stereoselectivity, high efficiency, and broad applicability for 10 types of sugars, with up to 89% yield and 53 examples.