Tartramide Ligands for Copper‐Catalyzed N‐Arylation at Room Temperature
| Autor: | Xuerui Ma, Robert P. Davies |
|---|---|
| Rok vydání: | 2022 |
| Předmět: |
MECHANISM
Science & Technology PALLADIUM RPKA Organic Chemistry Chemistry Organic 0904 Chemical Engineering BCL-2 General Chemistry 0305 Organic Chemistry Ullmann Reaction Chemistry Applied Chemistry AMINATION kinetics DISCOVERY Physical Sciences C-N bond formation 0302 Inorganic Chemistry COMPLEXES Copper |
| Zdroj: | Advanced Synthesis & Catalysis. 364:2023-2031 |
| ISSN: | 1615-4169 1615-4150 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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