Asymmetric Hydrogenation of Ketones with Polymer-Bound BINAP/Diamine Ruthenium Catalysts

Abstract

The BINAP/1,2‐diphenylethylenediamine RuCl2 complexes bound to a polystyrene resin act as precatalysts for asymmetric hydrogenation of various simple ketones. The enantioselectivity, turnover number, and turnover frequency are comparable to those attained under homogeneous conditions.

Synthesis of Chiral Catalysts Supported on Organic Polymers

“…Exactly the same route was followed by Noyori and co -workers in 2001 when they prepared an analogous polymerbound BINAP -diamine ruthenium catalyst for asymmetric reduction of ketones [15] . However, the crucial step in the synthesis of supported BINAP 11 is the clever regioselective acylation to give BINOL ether 8 , providing a point of polymer attachment at the BINOL that is located at some distance away from the fi nal catalytic center.…”

Design, Synthesis, Characterization of Novel Ruthenium(II) Catalysts: Highly Efficient and Selective Hydrogenation of Cinnamaldehyde to (E)-3-Phenylprop-2-en-1-ol

“…Ruthenium(II) complexes chelated with mixed diphosphine/diamine ligands have received much attention because of their potential application in the field of homogeneous catalysis [1,2,3,4,5,6,7,8,9]. In 1995, Noyori discovered that complexes derived from the parent [RuCl 2 (diphosphine) 2 (diamine) 2 ] can be utilized as homogeneous catalysts for the hydrogenation of α,β-unsaturated ketones [2,3,4].…”

Synthesis and Characterization of Novel Inorganic-Organic Hybrid Ru(II) Complexes and Their Application in Selective Hydrogenation

“…Our conceptual methodology was to take a homogeneous system of known catalytic behavior and, by performing suitable modifications, to tether this catalyst on silica supports, covalent anchoring of metal complexes on such surfaces being a topic of considerable interest in catalysis [ 20 , 22 ]. The desired hybrid materials are able to combine the advantages of homogeneous and heterogeneous catalysis: the catalyst becomes easily separable from the reaction products and it can be reused in several runs without an essential loss in the activity due to the leaching problem [ 23 , 24 , 25 , 26 ].…”