Fluorinated Alcohols as Solvents for Enantioselective Hydrogenation with Chiral Self-Assembling Rhodium Catalysts

Abstract

We herein describe the beneficial effect of fluorinated alcohols on asymmetric hydrogenation using chiral self-assembling rhodium complexes. Previously, the application of these catalysts has been hampered by low reaction rates in non-polar solvents, which are essential for establishing the self-assembling architecture via hydrogen bonding. Excellent reaction rates are usually observed in alcohols as solvents, but the characteristic hydrogen bonds are cleaved in those media, resulting in poor ee values. We now show for the first time that the disadvantageous properties of both solvent classes on the catalytic reaction can be overcome by using fluorinated alcohols. Due to this key finding, homogeneous catalysis with self-assembling catalysts is much closer to practical application.