Abstract
We report a Rh-catalyzed hydroamination of 1,3-dienes to generate homoallylic amines. Our work showcases the first case of anti-Markovnikov selectivity in the intermolecular coupling of amines and 1,3-dienes. By tuning the ligand properties and Brønsted acid additive, we find that a combination of rac-BINAP and mandelic acid is critical for achieving anti-Markovnikov selectivity.
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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Alkenes / chemical synthesis
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Alkenes / chemistry
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Allyl Compounds / chemical synthesis*
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Allyl Compounds / chemistry
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Amination
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Amines / chemical synthesis*
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Amines / chemistry
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Catalysis
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Ligands
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Mandelic Acids / chemical synthesis
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Mandelic Acids / chemistry
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Naphthalenes / chemical synthesis
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Naphthalenes / chemistry
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Rhodium / chemistry
Substances
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Alkenes
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Allyl Compounds
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Amines
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BINAP, 2-naphthol
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Ligands
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Mandelic Acids
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Naphthalenes
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Rhodium
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mandelic acid