Highly chemoselective transfer hydrogenation of the C[dbnd]C bonds of α-Keto substituted acrylate compounds catalyzed by an Iridium-TsEN complex in water

Abstract

Highly chemoselective transfer hydrogenation of the CC bonds of α-keto substituted acrylate compounds catalyzed by an [IrCl2Cp*]2-TsEN Complex (Cp* = η5-C5Me5) in water using sodium formate as hydride source has been developed. A variety of α-keto substituted acrylate compounds were reduced smoothly under 0.5 mol% of Iridium catalyst with 1.0 mol% ligand TsEN and 3 equiv. of sodium formate providing the desired product α-alkyl-β-keto esters in high to excellent yields (80–99 %). The procedure presented is simple and makes this method suitable for practical use.