Photoredox/Nickel-Catalyzed Cross-Coupling of Alkynyl Bromides and α-Silylamines for the Synthesis of Propynylamines

Propynylamines are prevalent structures widely existing in biologically active compounds and natural products. In this study, we present a novel alkynylation approach for synthesizing propargylamines by cross-coupling of alkynyl bromides and alpha-silylamines via a nickel metallaphotoredox catalysis. A diverse range of N-heterocyclic and acyclic alpha-silylamines, along with aromatic and aliphatic alkynyl bromides, are nicely incorporated, delivering structurally diverse propargylamines in moderate to good yields. Mechanistic studies suggest that the reaction proceeds through a radical pathway.