Tartramide Ligands for Copper‐Catalyzed N‐Arylation at Room Temperature
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.
- Standort
-
Deutsche Nationalbibliothek Frankfurt am Main
- Umfang
-
Online-Ressource
- Sprache
-
Englisch
- Erschienen in
-
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)
- Urheber
-
Ma, Xuerui
Davies, Robert P.
- DOI
-
10.1002/adsc.202200174
- URN
-
urn:nbn:de:101:1-2022052015011195545263
- Rechteinformation
-
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
-
15.08.2025, 07:33 MESZ
Datenpartner
Deutsche Nationalbibliothek. Bei Fragen zum Objekt wenden Sie sich bitte an den Datenpartner.
Beteiligte
- Ma, Xuerui
- Davies, Robert P.
Ähnliche Objekte (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
Room‐Temperature Copper‐Catalyzed Etherification of Aryl Bromides
Meta ‐Selective Copper‐Catalyzed C−H Arylation of Pyridines and Isoquinolines through Dearomatized Intermediates
On the Barton Copper‐Catalyzed C3‐Arylation of Indoles using Triarylbismuth bis (trifluoroacetate) Reagents
Meta ‐Selective Copper‐Catalyzed C−H Arylation of Pyridines and Isoquinolines through Dearomatized Intermediates
Copper-catalyzed asymmetric synthesis
Copper-Catalyzed Hydroarylation Reaction
Asymmetric Copper-Catalyzed Defluoroalkylation
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
Room‐Temperature Copper‐Catalyzed Etherification of Aryl Bromides
Meta ‐Selective Copper‐Catalyzed C−H Arylation of Pyridines and Isoquinolines through Dearomatized Intermediates
On the Barton Copper‐Catalyzed C3‐Arylation of Indoles using Triarylbismuth bis (trifluoroacetate) Reagents
Meta ‐Selective Copper‐Catalyzed C−H Arylation of Pyridines and Isoquinolines through Dearomatized Intermediates
Copper-catalyzed asymmetric synthesis
Copper-Catalyzed Hydroarylation Reaction
Asymmetric Copper-Catalyzed Defluoroalkylation
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
Room‐Temperature Copper‐Catalyzed Etherification of Aryl Bromides
Meta ‐Selective Copper‐Catalyzed C−H Arylation of Pyridines and Isoquinolines through Dearomatized Intermediates
On the Barton Copper‐Catalyzed C3‐Arylation of Indoles using Triarylbismuth bis (trifluoroacetate) Reagents
Meta ‐Selective Copper‐Catalyzed C−H Arylation of Pyridines and Isoquinolines through Dearomatized Intermediates
Copper-catalyzed asymmetric synthesis
Copper-Catalyzed Hydroarylation Reaction