Base-assisted transmetalation enables gold-catalyzed oxidative Sonogashira coupling reaction

Abstract

Summary: The traditional transition metal catalyzed neutral C(sp)-C(sp2) cross-coupling reaction between a nucleophile and an electrophile is a key technique for the formation of carbon-carbon bonds. Herein, we present a general gold-catalyzed oxidative Sonogashira cross-coupling of arylboronic acids and terminal arylalkynes at room temperature with excellent functional-group tolerance and good chemoselectivity. Moreover, our mechanistic studies suggested a third pathway involving a base-assisted transmetalation between the gold(I) catalyst and aryl boronic acid might predominate in our reaction conditions, rather than the previously assumed oxidation of the gold(I) complex or deprotonation of alkynes.

Keywords

• Chemistry
• Chemical reaction
• Catalysis