Immobilized Gold Nanoparticles Prepared from Gold(III)-Containing Ionic Liquids on Silica: Application to the Sustainable Synthesis of Propargylamines

A cycloaurated phosphinothioic amide gold(III) complex was supported on amorphous silica with the aid of an imidazolium ionic liquid (IL) physisorbed in the SiO(2) pores (SiO(2)–IL) and covalently bonded to the SiO(2) (SiO(2)@IL). Gold(0) nanoparticles (AuNPs) were formed in situ and subsequently immobilized on the SiO(2)–IL/SiO(2)@IL phase. The resulting catalytic systems Au–SiO(2)–IL and Au–SiO(2)@IL promoted the solvent-free A(3) coupling reaction of alkynes, aldehydes, and amines in high yields under solvent-free conditions with very low catalyst loading and without the use of additives. The Au–SiO(2)@IL catalyst showed good recyclability and could be reused at least five times with yields of propargylamines of ≥80%. This synthetic method provides a green and low cost way to effectively prepare propargylamines. Additionally, (31)P high resolution magic angle spinning (HRMAS) NMR spectroscopy is introduced as a simple technique to establish the Au loading of the catalyst.