Abstract
In the cross-coupling reactions of unprotected oxindoles with aryl halides, Pd- and Cu-based catalyst systems displayed orthogonal chemoselectivity. A Pd-dialkylbiarylphosphine-based catalyst system chemoselectively arylated oxindole at the 3 position, while arylation occurred exclusively at the nitrogen using a Cu-diamine-based catalyst system. Computational examination of the relevant L1Pd(Ar)(oxindolate) and diamine-Cu(oxindolate) species was performed to gain mechanistic insight into the controlling features of the observed chemoselectivity.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
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Research Support, U.S. Gov't, Non-P.H.S.
MeSH terms
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Benzene Derivatives / chemical synthesis
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Benzene Derivatives / chemistry*
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Catalysis
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Copper / chemistry*
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Hydrocarbons, Halogenated / chemistry
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Indoles / chemical synthesis
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Indoles / chemistry*
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Ligands
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Organometallic Compounds / chemistry
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Oxindoles
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Palladium / chemistry*
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Pyrrolidinones / chemical synthesis
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Pyrrolidinones / chemistry
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Thermodynamics
Substances
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Benzene Derivatives
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Hydrocarbons, Halogenated
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Indoles
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Ligands
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Organometallic Compounds
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Oxindoles
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Pyrrolidinones
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2-oxindole
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Palladium
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Copper