Stereocontrolled Synthesis of Aryl <i>C</i>-Nucleosides under Ambient Conditions

Abstract

A stereocontrolled synthesis of an aryl <i>C</i>-nucleoside has been developed using D-ribals and arylboronic acids catalyzed by palladium without additional ligands in common solvents under an open-air atmosphere at room temperature. This protocol features very mild conditions, simplicity in operation, exclusive β-stereoselectivity, broad substrate scopes, and good compatibility with reactive amino and hydroxyl groups. The functionalization of unsaturated <i>C</i>-nucleosides and the late-stage glycosylation of natural products/drugs demonstrated the high practicality of this strategy.