Palladium(II)-Catalyzed Heck Coupling: Direct Stereoselective Synthesis of C-Aryl Glycosides from Nonactivated Glycals and Thianthrenium Salts

Org Lett. 2024 Mar 29;26(12):2473-2477. doi: 10.1021/acs.orglett.4c00654. Epub 2024 Mar 18.

Abstract

Here, we report an efficient Pd(II)-catalyzed Heck coupling reaction utilizing modular and readily available thianthrenium salts. The tunability and ease of thianthrenium salts facilitated the integration of glycals with drugs, natural products, and peptides. This method allows the incorporation of diverse glycals into structurally varied aglycon components without directing groups or prefunctionalization and provides a practical method for synthesizing C-aryl glycosides, offering a new avenue for the production of complex glycosides with potential applications.