Graphite oxide as support for the immobilization of Ru-BINAP: Application in the enantioselective hydrogenation of methylacetoacetate

Graphite oxide (GO), previously functionalized with an alkoxysilane or with an isocyanate, and a chiral amine, was used as support for the immobilization of the homogeneous Ru-BINAP complex. The functionalized supports and the hybrid catalysts were characterized by XRD, NMR, TG, DRIFTS and XPS techniques. Among the hybrid catalysts the more active and enantioselective in the hydrogenation of methyl acetoacetate is the sample prepared over the non-functionalized GO. The catalytic performance can be interpreted in terms of the metal complex interacting with the oxygen functional groups or with the chiral amine at its different locations, anchored covalently onto the Cl pendant positions or via acid-base interaction at the oxygen functional groups. (C) 2012 Elsevier B.V. All rights reserved.