Exhaustive Reduction of Esters Enabled by Nickel Catalysis
Adam Cook, Sekar Prakash, Yan‐Long Zheng, Stephen G. Newman
Abstract
We report a one-step procedure to directly reduce unactivated aryl esters into their corresponding tolyl derivatives. This is achieved by an organosilane-mediated ester hydrosilylation reaction and subsequent Ni/NHC-catalyzed hydrogenolysis. The resulting conditions provide a direct and efficient alternative to multi-step procedures for this transformation that often require the use of hazardous metal hydrides. Applications in the synthesis of −CD3-containing products, derivatization of bioactive molecules, and chemoselective reduction in the presence of other C–O bonds are demonstrated.
Topics & Concepts
ChemistryHydrogenolysisDerivatizationHydrosilylationArylCatalysisNickelCombinatorial chemistryChemoselectivityMoleculeOrganic chemistryReduction (mathematics)AlkylGeometryMathematicsHigh-performance liquid chromatographyAsymmetric Hydrogenation and CatalysisCatalytic Cross-Coupling ReactionsChemical Synthesis and Analysis