Tartramide ligands for copper-catalyzed N-Arylation at room temperature
Author(s)
Davies, Robert
Ma, Xuerui
Type
Journal Article
Abstract
Abstract. A novel class of readily accessible tartramide ligands has 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, gives excellent conversions 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.
Date Issued
2022-05-09
Date Acceptance
2022-05-09
Citation
Advanced Synthesis and Catalysis, 2022, 364 (12)
ISSN
1615-4150
Publisher
Wiley
Journal / Book Title
Advanced Synthesis and Catalysis
Volume
364
Issue
12
Copyright Statement
© 2022 The Authors.AdvancedSynthesis& Catalysispublishedby Wiley-VCHGmbH.This is an open access article under theterms of the CreativeCommonsAttributionLicense,which permitsuse, distributionand reproductionin any medium,providedthe originalwork is properlycited.
License URL
Identifier
https://onlinelibrary.wiley.com/doi/abs/10.1002/adsc.202200174
Subjects
Science & Technology
Physical Sciences
Chemistry, Applied
Chemistry, Organic
Chemistry
Copper
Ullmann Reaction
C-N bond formation
kinetics
RPKA
COMPLEXES
AMINATION
PALLADIUM
DISCOVERY
MECHANISM
BCL-2
0302 Inorganic Chemistry
0305 Organic Chemistry
0904 Chemical Engineering
Organic Chemistry
Publication Status
Published online
Date Publish Online
2022-05-09