Tartramide Ligands for Copper‐Catalyzed N‐Arylation at Room Temperature

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Abstract: Readily accessible tartramide ligands have been demonstrated to promote copper‐catalysed N‐arylation under mild conditions. In addition, the coupling protocol employs cheap and readily available pre‐catalyst, ligand, and base (NaOH), and overcomes many current limitations often associated with Ullmann coupling: it can be run with low catalyst loadings, does not require the use of excess amine, operates at room temperature, is fully homogeneous, and displays improved tolerance to air and moisture. Detailed kinetic studies using reaction progress kinetic analysis (RPKA) methods have provided insight into the factors influencing the reaction rate in terms of impact of ligand structure, reactant/catalyst dependence and catalyst (in) stability. These kinetic insights have been used in a quality‐by‐design approach for further optimization of the reaction protocol. The reaction scope was extended to 22 examples, showing broad applicability for a wide range of substituted aryl iodides with both primary and secondary amines.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Tartramide Ligands for Copper‐Catalyzed N‐Arylation at Room Temperature ; day:19 ; month:05 ; year:2022 ; extent:1
Advanced synthesis & catalysis ; (19.05.2022) (gesamt 1)

Creator: Ma, Xuerui
Davies, Robert P.

DOI: 10.1002/adsc.202200174

URN: urn:nbn:de:101:1-2022052015011195545263

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

Last update: 15.08.2025, 7:33 AM CEST

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Ma, Xuerui
Davies, Robert P.

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Tartramide Ligands for Copper‐Catalyzed N‐Arylation at Room Temperature

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Other Objects (12)

Mild Conditions for Copper-Catalyzed N-Arylation of Imidazoles

Copper-catalyzed arylation of alkyl halides with arylaluminum reagents

Copper-catalyzed remote C–H arylation of polycyclic aromatic hydrocarbons (PAHs)

Copper-catalyzed N-arylation of amines with aryliodonium ylides in water

Room‐Temperature Copper‐Catalyzed Etherification of Aryl Bromides

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Copper-catalyzed remote C–H arylation of polycyclic aromatic hydrocarbons (PAHs)

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Room‐Temperature Copper‐Catalyzed Etherification of Aryl Bromides

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Copper-Catalyzed Hydroarylation Reaction

Asymmetric Copper-Catalyzed Defluoroalkylation

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