ACS Catalysis · 2021 · 42 citations · 61 references
Natural SciencesChemical EngineeringChemistryCatalysisOrganic ChemistryOrganometallic ChemistryCatalyst DesignCatalyst SynthesisCatalytic MechanismsLigand BindingMetal-ligand BondingTemplate-directed SynthesisAromatic Carbonyl ChemistryC - H Bond FunctionalizationCatalytic FunctionalizationHeterocycle FunctionalizationPalladium CatalystsSite-selective FunctionalizationTransition-metal-catalyzed Functionalization
Controlling positional selectivity represents one of the most important aspects in transition-metal-catalyzed C–H bond functionalization. However, the conventional directing template strategies via a covalent binding to the substrates are always hindered by prior stoichiometric installation and removal of the directing groups. Herein, we report a palladium-catalyzed meta-selective C–H olefination of aromatic carbonyl compounds by noncovalent hydrogen-bonding interaction. N,N′-Substituted ureas were engineered to serve as a H-bonding donor for binding to the substrates and, meanwhile, achieve site-selective control by the integrated directing group.
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