Chiral alcohols are essential starting materials in the advancement of pharmaceutical and industrial technologies. Developing new environmentally sustainable methods to generate chiral alcohols by the reduction of ketone functional groups is industrially important. Here we report our efforts to conduct asymmetrical hydrogenation of ketones using a nickel(ll) N-heterocyclic carbene (NHC) hybrid complex in aqueous conditions. Hybrid catalytic systems use chiral biomolecules linked to catalytic systems to steer substrate/catalyst interactions to afford some enantiomeric selection. Here we report the synthesis and characterization of a series of Ni-NHC complexes using UV-Vis spectroscopy, HR-MS techniques, and X-ray crystallography. The catalytic efficiency of these Ni-NHC systems were optimized by varying reaction time, catalyst loading, reducing agents, and solvent. Once suitable conditions were found, these planar NI-NHC complexes were used in the presence of several different DNA samples (ST-DNA, CT-DNA, and several DNA constructs) to generate a DNA/Ni-NHC hybrid system for chiral ketone reduction.

Nickel N-heterocyclic carbene complexes and their applications in asymmetric hydrogenation of ketones

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