Synthesis and catalytic applications of 1,2,3-triazolylidene gold(I) complexes in silver-free oxazoline syntheses and C-H bond activation

Abstract

A series of novel 1,2,3-triazolylidene gold(I) chloride complexes have been synthesised and fully characterised. Silver-free methodologies for chloride ion abstraction of these complexes were evaluated for their potential as Au-based catalyst precursors. Using simple potassium salts or MeOTf as chloride scavengers produced metal complexes that catalyse both the regioselective synthesis of oxazolines and the C-H activation of benzene or styrene for carbene transfer from ethyl diazoacetate. These results indicate that Ag-free activation of 1,2,3-triazolylidene gold(I) chloride complexes is feasible for the generation of catalytically active Au triazolylidene species. However, silver-mediated activation imparts substantially higher catalytic activity in oxazoline synthesis.