Ruthenium-arene complexes bearing imidazol(in)ium-2-dithiocarboxylate ligands: Evaluation of their catalytic activity in the synthesis of enol esters

The catalytic activity of four ruthenium imidazol(in)ium-2-dithiocarboxylates was evaluated for the synthesis of vinyl esters through addition of 4-acetoxybenzoic acid to 1-hexyne, and compared to those of the parent ruthenium-N-heterocyclic carbene complexes and [RuCl2(p-cymene)(PPh3)] (a standard catalyst). It turned out that ruthenium imidazol(in)ium-2-dithiocarboxylates were poorly active and selective. Quantitative yields, indeed, were obtained only after extended reaction times. However, the catalytic activity could be improved significantly under microwave heating or conventional heating in a sealed tube at 160 degrees C, driving the reaction to completion in less than 4 h of reaction. (C) 2009 Elsevier B. V. All rights reserved.