Palladium-Catalyzed Room Temperature Acylative Cross-Coupling of Activated Amides with Trialkylboranes
Abstract
:1. Introduction
2. Results and Discussion
3. Materials and Methods
3.1. General
3.2. General Procedure for the PEPPSI-Catalyzed Cross-Coupling of N-Methyl-N-Tosylamides with Trialkylboranes
4. Conclusions
Supplementary Materials
Author Contributions
Conflicts of Interest
References
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Sample Availability: Samples of the compounds are available from the authors. |
Entry | Equiv of 2a | Solvent | Base b | T (°C) | Time (h) | Yield (%) c |
---|---|---|---|---|---|---|
1 | 1.1 | THF | K2CO3 | 60 | 5 | 61 |
2 | 1.1 | THF | / | 60 | 5 | NR d |
3 | 1.1 | THF | Cs2CO3 | 60 | 5 | 25 |
4 | 1.1 | THF | K3PO4 | 60 | 5 | 33 |
5 | 1.1 | THF | Na2CO3 | 60 | 8 | 15 |
6 | 1.1 | THF | NaHCO3 | 60 | 8 | Trace d |
7 | 1.1 | THF | NaOAc | 60 | 8 | Trace d |
8 | 1.1 | THF | Et3N | 60 | 8 | NR d |
9 | 1.1 | THF | Pyridine | 60 | 8 | NR d |
10 | 1.5 | THF | K2CO3 | 60 | 5 | 80 |
11 | 1.5 | Dioxane | K2CO3 | 60 | 8 | 35 |
12 | 1.5 | MTBE | K2CO3 | 55 | 8 | 90 |
13 | 1.5 | MeCN | K2CO3 | 60 | 8 | 17 |
14 | 1.5 | MTBE | K2CO3 | rt | 24 | 98 |
15 | 1.5 | MTBE | K3PO4 | rt | 24 | 84 |
16 | 1.5 | THF | K2CO3 | rt | 24 | 82 |
17 | 1.5 | THF | K3PO4 | rt | 12 | 40 |
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Shi, W.; Zou, G. Palladium-Catalyzed Room Temperature Acylative Cross-Coupling of Activated Amides with Trialkylboranes. Molecules 2018, 23, 2412. https://doi.org/10.3390/molecules23102412
Shi W, Zou G. Palladium-Catalyzed Room Temperature Acylative Cross-Coupling of Activated Amides with Trialkylboranes. Molecules. 2018; 23(10):2412. https://doi.org/10.3390/molecules23102412
Chicago/Turabian StyleShi, Weijia, and Gang Zou. 2018. "Palladium-Catalyzed Room Temperature Acylative Cross-Coupling of Activated Amides with Trialkylboranes" Molecules 23, no. 10: 2412. https://doi.org/10.3390/molecules23102412