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Updated: Jul 8, 2025

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Base-assisted transmetalation enables gold-catalyzed oxidative Sonogashira coupling reaction
Lizhu Zhang1, Wenchao Zhang1, Dinghua Li1
1School of Materials Science & Engineering, Beijing Institute of Technology, Beijing 100081, China.
Abstract:
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.
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