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

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Abstract: The aryloxyamine motif is a prominent pharmacophore in drug design and development. While these biologically relevant structures could in principle be sustainably assembled from the base metal‐catalyzed O‐arylation of inexpensive and abundant amino alcohols with (hetero) aryl chlorides, reports of such challenging C−O bond formations with useful scope are lacking. In response, we report herein the hitherto unknown Ni‐catalyzed C−O cross‐coupling of N‐protected amino alcohols (primary, secondary, and tertiary) with (hetero) aryl chlorides. Also presented are chemoselective sequential/telescoped C−N and C−O cross‐couplings of the unprotected amino alcohol prolinol to afford an unsymmetrical diarylated product.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Nickel‐Catalyzed O ‐Arylation of N ‐Protected Amino Alcohols with (Hetero) aryl Chlorides ; day:08 ; month:12 ; year:2024 ; extent:7
Chemistry - a European journal ; (08.12.2024) (gesamt 7)

Creator: Morrison, Kathleen M.
Jackson, Emily C.
Elliott, Erika M. H.
Stradiotto, Mark

DOI: 10.1002/chem.202404352

URN: urn:nbn:de:101:1-2412091412276.950866031093

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

Last update: 15.08.2025, 7:34 AM CEST

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Morrison, Kathleen M.
Jackson, Emily C.
Elliott, Erika M. H.
Stradiotto, Mark

Other Objects (12)

Nickel‐Catalyzed Chemoselective Arylation of Amino Alcohols

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Nickel-Catalyzed Synthesis of γ-Fluorinated Homoallylic Alcohols

Nickel‐Catalyzed Reductive Hydrolysis of Nitriles to Alcohols

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

Nickel‐Catalyzed Electrochemical Synthesis of (Hetero) Aryl Trifluoromethyl Selenides

Room Temperature, Metal‐Free Arylation of Aliphatic Alcohols

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

Difluoromethylation of (hetero)aryl chlorides with chlorodifluoromethane catalyzed by nickel

Nickel‐Catalyzed Chemoselective Arylation of Amino Alcohols

Ligand Relay for Nickel‐Catalyzed Decarbonylative Alkylation of Aroyl Chlorides

Photochemical (Hetero-)Arylation of Aryl Sulfonium Salts

Nickel-Catalyzed Synthesis of γ-Fluorinated Homoallylic Alcohols

Nickel‐Catalyzed Reductive Hydrolysis of Nitriles to Alcohols

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

Nickel‐Catalyzed Electrochemical Synthesis of (Hetero) Aryl Trifluoromethyl Selenides

Room Temperature, Metal‐Free Arylation of Aliphatic Alcohols

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

Difluoromethylation of (hetero)aryl chlorides with chlorodifluoromethane catalyzed by nickel

Nickel‐Catalyzed Chemoselective Arylation of Amino Alcohols

Ligand Relay for Nickel‐Catalyzed Decarbonylative Alkylation of Aroyl Chlorides

Photochemical (Hetero-)Arylation of Aryl Sulfonium Salts

Nickel-Catalyzed Synthesis of γ-Fluorinated Homoallylic Alcohols

Nickel‐Catalyzed Reductive Hydrolysis of Nitriles to Alcohols

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

Nickel‐Catalyzed Electrochemical Synthesis of (Hetero) Aryl Trifluoromethyl Selenides

Room Temperature, Metal‐Free Arylation of Aliphatic Alcohols

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

Difluoromethylation of (hetero)aryl chlorides with chlorodifluoromethane catalyzed by nickel

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

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Other Objects (12)

Nickel‐Catalyzed Chemoselective Arylation of Amino Alcohols

Nickel‐Catalyzed Chemoselective Arylation of Amino Alcohols

Ligand Relay for Nickel‐Catalyzed Decarbonylative Alkylation of Aroyl Chlorides

Photochemical (Hetero-)Arylation of Aryl Sulfonium Salts

Nickel-Catalyzed Synthesis of γ-Fluorinated Homoallylic 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

Nickel‐Catalyzed Electrochemical Synthesis of (Hetero) Aryl Trifluoromethyl Selenides

Room Temperature, Metal‐Free Arylation of Aliphatic Alcohols

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

Difluoromethylation of (hetero)aryl chlorides with chlorodifluoromethane catalyzed by nickel

Nickel‐Catalyzed Chemoselective Arylation of Amino Alcohols

Nickel‐Catalyzed Chemoselective Arylation of Amino Alcohols

Ligand Relay for Nickel‐Catalyzed Decarbonylative Alkylation of Aroyl Chlorides

Photochemical (Hetero-)Arylation of Aryl Sulfonium Salts

Nickel-Catalyzed Synthesis of γ-Fluorinated Homoallylic 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

Nickel‐Catalyzed Electrochemical Synthesis of (Hetero) Aryl Trifluoromethyl Selenides

Room Temperature, Metal‐Free Arylation of Aliphatic Alcohols

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

Difluoromethylation of (hetero)aryl chlorides with chlorodifluoromethane catalyzed by nickel

Nickel‐Catalyzed Chemoselective Arylation of Amino Alcohols

Nickel‐Catalyzed Chemoselective Arylation of Amino Alcohols

Ligand Relay for Nickel‐Catalyzed Decarbonylative Alkylation of Aroyl Chlorides

Photochemical (Hetero-)Arylation of Aryl Sulfonium Salts

Nickel-Catalyzed Synthesis of γ-Fluorinated Homoallylic 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

Nickel‐Catalyzed Electrochemical Synthesis of (Hetero) Aryl Trifluoromethyl Selenides

Room Temperature, Metal‐Free Arylation of Aliphatic Alcohols

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

Difluoromethylation of (hetero)aryl chlorides with chlorodifluoromethane catalyzed by nickel

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