UVA LED Light Promoted Cross-Coupling of Tertiary a-Silylamines with 1-Iodoalkynes

A synthetic strategy that exploits the formation of an electron donor-acceptor (EDA) complex between a tertiary a-silylamine and 1-iodoalkyne under UVA LED (light emitting diode) light (?(max)=365 nm) to prepare propargyl amines is described. The site- and chemoselective synthetic method was shown to tolerate a wide range of functional groups to give the a-alkynylation product in good to excellent yields. The usefulness of the C(sp)-C(sp(3)) bond formation protocol was also exemplified by the late-stage functionalisation of a variety of natural products and bioactive compounds.