Angewandte Chemie International Edition · 2014 · 128 citations · 66 references
Natural SciencesChemistryCatalysisGreen ChemistryOrganic ChemistryCatalyst DesignCatalyst PreparationCross-coupling ReactionsDiversity-oriented SynthesisHeterocycle SynthesisOrganic SynthesisActivated CarbonDirect ReplacementHeterocycle FunctionalizationNucleophile ReactivityOrganolithium CompoundsTransition Metal-catalyzed SynthesisTransition-metal-catalyzed Cross-couplingTransition-metal-catalyzed Functionalization
The direct replacement of aromatic methoxy groups with activated carbon nucleophiles would give rise to novel synthetic pathways for targeted and diversity-oriented syntheses. We demonstrate here that this transformation can be achieved in a one-step reaction involving a bifunctional organolithium nucleophile in combination with a CAr OMe bond-cleaving nickel catalyst. The resulting products are stable, α-CH active, and suitable for various further modifications.
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Selective, Nickel-Catalyzed Hydrogenolysis of Aryl Ethers
Alexey G. Sergeev, John F. Hartwig · Science · 2011 · 835 citations