Nickel‐Catalyzed Chemoselective Arylation of Amino Alcohols

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Abstract: A systematic evaluation of competitive bisphosphine/Ni‐catalyzed C−N versus C−O cross‐couplings involving model compounds enabled development of hitherto unknown chemoselective O‐ and N‐arylation of amino alcohols with (hetero) aryl chloride electrophiles, without recourse to protection group chemistry. Use of the CyPAd‐DalPhos pre‐catalyst C2 enabled particularly challenging O‐arylation chemoselectivity in amino alcohols featuring branched primary and secondary alkylamine groups, while selective N‐arylation was observed in substrates featuring less‐hindered linear alkylamine and aniline reacting groups. Useful reaction scope in the (hetero) aryl chloride was achieved throughout, and the ability to conduct such transformations using benchtop handling of materials is demonstrated.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Nickel‐Catalyzed Chemoselective Arylation of Amino Alcohols ; day:26 ; month:04 ; year:2023 ; extent:7
Angewandte Chemie / International edition. International edition ; (26.04.2023) (gesamt 7)

Creator: Morrison, Kathleen M.
Yeung, Charles S.
Stradiotto, Mark

DOI: 10.1002/anie.202300686

URN: urn:nbn:de:101:1-2023042715171010842429

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 14.08.2025, 11:00 AM CEST

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Associated

Morrison, Kathleen M.
Yeung, Charles S.
Stradiotto, Mark

Other Objects (12)

Nickel‐Catalyzed Chemoselective Arylation of Amino Alcohols

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Nickel‐Catalyzed O ‐Arylation of N ‐Protected Amino Alcohols with (Hetero) aryl Chlorides

Nickel‐Catalyzed O ‐Arylation of N ‐Protected Amino Alcohols with (Hetero) aryl Chlorides

Nickel-Catalyzed Synthesis of γ-Fluorinated Homoallylic Alcohols

Nickel-Catalyzed Synthesis of γ-Fluorinated Homoallylic Alcohols

Nickel‐Catalyzed Reductive Hydrolysis of Nitriles to Alcohols

Nickel‐Catalyzed Reductive Hydrolysis of Nitriles to Alcohols

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Nickel‐Catalyzed Reductive Hydrolysis of Nitriles to Alcohols

Electrochemically Driven Nickel‐Catalyzed Enantioselective Hydro‐Arylation/Alkenylation of Enones

Electrochemically Driven Nickel‐Catalyzed Enantioselective Hydro‐Arylation/Alkenylation of Enones

Nickel‐Catalyzed Inter‐ and Intramolecular Aryl Thioether Metathesis by Reversible Arylation

Nickel‐Catalyzed Inter‐ and Intramolecular Aryl Thioether Metathesis by Reversible Arylation

Nickel‐Catalyzed C sp2 −OMe Functionalization for Chemoselective Aromatic Homologation En Route to Nanographenes

Nickel‐Catalyzed C sp2 −OMe Functionalization for Chemoselective Aromatic Homologation En Route to Nanographenes

Copper/Aluminum Hydrotalcite Catalyzed O-Arylation of Phenols/Alcohols with Aryl Halides

Copper/Aluminum Hydrotalcite Catalyzed O-Arylation of Phenols/Alcohols with Aryl Halides

Nickel-Catalyzed Multicomponent Connection

Nickel-Catalyzed Multicomponent Connection

Nickel-Catalyzed Heck Reaction

Nickel-Catalyzed Heck Reaction

Exogenous Ligand‐Free Nickel‐Catalyzed Carboxylate O ‐Arylation: Insight into Ni I/Ni III Cycles **

Exogenous Ligand‐Free Nickel‐Catalyzed Carboxylate O ‐Arylation: Insight into Ni I/Ni III Cycles **

Nickel‐Catalyzed Chemoselective Arylation of Amino Alcohols

Nickel‐Catalyzed Chemoselective Arylation of Amino Alcohols

Nickel‐Catalyzed O ‐Arylation of N ‐Protected Amino Alcohols with (Hetero) aryl Chlorides

Nickel‐Catalyzed O ‐Arylation of N ‐Protected Amino Alcohols with (Hetero) aryl Chlorides

Nickel-Catalyzed Synthesis of γ-Fluorinated Homoallylic Alcohols

Nickel-Catalyzed Synthesis of γ-Fluorinated Homoallylic Alcohols

Nickel‐Catalyzed Reductive Hydrolysis of Nitriles to Alcohols

Nickel‐Catalyzed Reductive Hydrolysis of Nitriles to Alcohols

Nickel‐Catalyzed Reductive Hydrolysis of Nitriles to Alcohols

Nickel‐Catalyzed Reductive Hydrolysis of Nitriles to Alcohols

Electrochemically Driven Nickel‐Catalyzed Enantioselective Hydro‐Arylation/Alkenylation of Enones

Electrochemically Driven Nickel‐Catalyzed Enantioselective Hydro‐Arylation/Alkenylation of Enones

Nickel‐Catalyzed Inter‐ and Intramolecular Aryl Thioether Metathesis by Reversible Arylation

Nickel‐Catalyzed Inter‐ and Intramolecular Aryl Thioether Metathesis by Reversible Arylation

Nickel‐Catalyzed C sp2 −OMe Functionalization for Chemoselective Aromatic Homologation En Route to Nanographenes

Nickel‐Catalyzed C sp2 −OMe Functionalization for Chemoselective Aromatic Homologation En Route to Nanographenes

Copper/Aluminum Hydrotalcite Catalyzed O-Arylation of Phenols/Alcohols with Aryl Halides

Copper/Aluminum Hydrotalcite Catalyzed O-Arylation of Phenols/Alcohols with Aryl Halides

Nickel-Catalyzed Multicomponent Connection

Nickel-Catalyzed Multicomponent Connection

Nickel-Catalyzed Heck Reaction

Nickel-Catalyzed Heck Reaction

Exogenous Ligand‐Free Nickel‐Catalyzed Carboxylate O ‐Arylation: Insight into Ni I/Ni III Cycles **

Exogenous Ligand‐Free Nickel‐Catalyzed Carboxylate O ‐Arylation: Insight into Ni I/Ni III Cycles **

Nickel‐Catalyzed Chemoselective Arylation of Amino Alcohols

Nickel‐Catalyzed Chemoselective Arylation of Amino Alcohols

Nickel‐Catalyzed O ‐Arylation of N ‐Protected Amino Alcohols with (Hetero) aryl Chlorides

Nickel‐Catalyzed O ‐Arylation of N ‐Protected Amino Alcohols with (Hetero) aryl Chlorides

Nickel-Catalyzed Synthesis of γ-Fluorinated Homoallylic Alcohols

Nickel-Catalyzed Synthesis of γ-Fluorinated Homoallylic Alcohols

Nickel‐Catalyzed Reductive Hydrolysis of Nitriles to Alcohols

Nickel‐Catalyzed Reductive Hydrolysis of Nitriles to Alcohols

Nickel‐Catalyzed Reductive Hydrolysis of Nitriles to Alcohols

Nickel‐Catalyzed Reductive Hydrolysis of Nitriles to Alcohols

Electrochemically Driven Nickel‐Catalyzed Enantioselective Hydro‐Arylation/Alkenylation of Enones

Electrochemically Driven Nickel‐Catalyzed Enantioselective Hydro‐Arylation/Alkenylation of Enones

Nickel‐Catalyzed Inter‐ and Intramolecular Aryl Thioether Metathesis by Reversible Arylation

Nickel‐Catalyzed Inter‐ and Intramolecular Aryl Thioether Metathesis by Reversible Arylation

Nickel‐Catalyzed C sp2 −OMe Functionalization for Chemoselective Aromatic Homologation En Route to Nanographenes

Nickel‐Catalyzed C sp2 −OMe Functionalization for Chemoselective Aromatic Homologation En Route to Nanographenes

Copper/Aluminum Hydrotalcite Catalyzed O-Arylation of Phenols/Alcohols with Aryl Halides

Copper/Aluminum Hydrotalcite Catalyzed O-Arylation of Phenols/Alcohols with Aryl Halides

Nickel-Catalyzed Multicomponent Connection

Nickel-Catalyzed Multicomponent Connection

Nickel-Catalyzed Heck Reaction

Nickel-Catalyzed Heck Reaction

Exogenous Ligand‐Free Nickel‐Catalyzed Carboxylate O ‐Arylation: Insight into Ni I/Ni III Cycles **

Exogenous Ligand‐Free Nickel‐Catalyzed Carboxylate O ‐Arylation: Insight into Ni I/Ni III Cycles **

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