Gold(i)-catalyzed addition of carboxylic acids to internal alkynes in aqueous medium

Abstract

We report herein the efficient hydro-oxycarbonylation of symmetrical and unsymmetrical internal alkynes with carboxylic acids in water at 60 °C, employing the catalytic system [AuCl(PPh₃)]/AgOAc (5 mol%). This simple and eco-friendly protocol allows for the synthesis of a wide variety of trisubstituted enol esters (37 examples) in high yields and with complete Z-stereoselectivity. The use of microwave irradiation as an alternative energy source has also been evaluated.