Recovery and Recycling of Chiral Iridium(N,P Ligand) Catalysts from Hydrogenation Reactions

Despite the high efficiency and broad scope of chiral iridium(N,P ligand) complexes as catalysts for asymmetric hydrogenation, the problem of catalyst recovery and recycling has so far attracted little attention. We have found that at the end of a hydrogenation reaction, iridium(N,P ligand) catalysts form dimeric Ir(III) dihydride complexes, which can be converted back to the original precatalysts by addition of COD. Based on these findings, a practically simple protocol for catalyst recovery was devised. The recovered complexes showed essentially the same reactivity and enantioselectivity as the original catalysts. Especially large-scale applications and hydrogenations of less reactive substrates that require high catalyst loadings will benefit from this protocol that allows recovery and reuse of expensive iridium complexes.