Abstract
A palladium-catalyzed, norbornene-mediated ortho-alkylation reaction of aryl iodides with secondary alkyl halides is described. Intermolecular or intramolecular ortho-alkylation proceeds in a domino process with various termination steps, generating two new carbon-carbon or carbon-nitrogen bonds in one pot, to afford an array of polycyclic heterocycles. The use of enantioenriched substrates has shown that this palladium-catalyzed reaction is stereospecific, proceeding with minimal erosion of ee.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Alkylation
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Catalysis
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Heterocyclic Compounds / chemical synthesis*
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Heterocyclic Compounds / chemistry
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Hydrocarbons, Halogenated / chemistry*
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Molecular Structure
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Norbornanes / chemistry
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Palladium / chemistry
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Polycyclic Aromatic Hydrocarbons / chemical synthesis*
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Polycyclic Aromatic Hydrocarbons / chemistry
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Stereoisomerism
Substances
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Heterocyclic Compounds
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Hydrocarbons, Halogenated
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Norbornanes
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Polycyclic Aromatic Hydrocarbons
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Palladium