Journal of the American Chemical Society · 2013 · 318 citations · 80 references
Natural SciencesChemistryCatalysisOrganic ChemistryOrganometallic ChemistryCatalyst DesignCatalytic MechanismsHeterocycle SynthesisOrganic SynthesisActive Site SelectivityArene FunctionalizationC - H Bond FunctionalizationFunctional Group ToleranceHeterocycle FunctionalizationOrganometallic CatalysisSite-selective FunctionalizationStereoselective Amination
A Pd and norbornene-catalyzed ortho-arene amination via Catellani-type C-H functionalization is reported. Aryl halides are used as substrates; N-benzoyloxyamines and isopropanol are employed as the amine source (oxidant) and reductant respectively. Examples are provided in 50-99% yields with high functional group tolerance. This method gives complementary site selectivity at the ortho- instead of ipso-position of aryl halides.
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