Gold-catalyzed azidation, cyanation, and alkynylation of aryl iodides from readily available TMS-N3, TMS-CN, and alkynyl-TMS

Abstract

We have developed a unified protocol for gold-catalyzed azidation, cyanation, and alkynylation of aryl iodides from readily available silane-based nucleophiles (Nu-TMS) such as TMS-N₃, TMS-CN, and alkynyl-TMS. The key step is the activation of Nu-TMS by a suitable silver activator to generate reactive Ag–Nu intermediates. The reaction is based on readily available starting materials (eliminating the need for toxic reagents such as NaN₃ and KCN), a broad substrate scope, and straightforward conditions (no requirement for air- or water-free conditions).