Oxygen-Free Csp3-H Oxidation of Pyridin-2-yl-methanes to Pyridin-2-yl-methanones with Water by Copper Catalysis
Abstract
:1. Introduction
2. Results and Discussion
3. Materials and Methods
3.1. General Information
3.2. General Procedure for the Synthesis of 2
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Entry | Cu Salt (mol %) | Water | Solvent | Time/h | Yield/% |
---|---|---|---|---|---|
1 | Cu(NO3)2·3H2O (10 mol%) | 5.0 equiv. | DMA | 20 | 69 |
2 | Cu(NO3)2·3H2O (10 mol%) | 2.5 equiv. | DMA | 20 | 68 |
3 | Cu(NO3)2·3H2O (10 mol%) | - | DMA | 20 | 36 |
4 | Cu(NO3)2 (10 mol%) | - | DMA | 20 | 8 |
5 | Cu(NO3)2 (10 mol%) | 2.5 equiv. | DMA | 20 | 59 |
6 | Cu(NO3)2·3H2O (10 mol%) | 2.5 equiv. | DMA | 20 | 70 b |
7 | Cu(NO3)2·3H2O (10 mol%) | 2.5 equiv. | DMA | 20 | 43 c |
8 | Cu(NO3)2·3H2O (10 mol%) | 2.5 equiv. | DMA | 12 | 41 |
9 | Cu(NO3)2·3H2O (10 mol%) | 2.5 equiv. | DMA | 30 | 61 |
10 | Cu(NO3)2·3H2O (5 mol%) | 2.5 equiv. | DMA | 20 | 40 |
11 | Cu(NO3)2·3H2O (20 mol%) | 2.5 equiv. | DMA | 20 | 68 |
12 | Cu(OAc)·H2O (10 mol%) | 2.5 equiv. | DMA | 20 | 42 |
13 | CuCl2·2H2O (10 mol%) | 2.5 equiv. | DMA | 20 | 45 |
14 | CuSO4 (10 mol%) | 2.5 equiv. | DMA | 20 | 36 |
15 | CuBr2 (10 mol%) | 2.5 equiv. | DMA | 20 | 40 |
16 | Cu(CF3SO3)2 (10 mol%) | 2.5 equiv. | DMA | 20 | 22 |
17 | Cu(NO3)2·3H2O (10 mol%) | 2.5 equiv. | DMF | 20 | 45 |
18 | Cu(NO3)2·3H2O (10 mol%) | 2.5 equiv. | DMSO | 20 | 30 |
19 | Cu(NO3)2·3H2O (10 mol%) | 2.5 equiv. | NMP | 20 | 21 |
20 | Cu(NO3)2·3H2O (10 mol%) | 2.5 equiv. | PhCl | 20 | 23 |
21 | Cu(NO3)2·3H2O (10 mol%) | 2.5 equiv. | Et3N | 20 | trace |
22 | Cu(NO3)2·3H2O (10 mol%) | 2.5 equiv. | H2O | 20 | trace |
Entry | 1 | Ar | Time/h | 2 | Yield/% |
---|---|---|---|---|---|
1 | 1a–1o | Ph | 20 | 2a | 68 |
2 | 4-t-BuC6H4 | 38 | 2b | 76 | |
3 | 2-naphthyl | 30 | 2c | 85 | |
4 | 4-PhC6H4 | 30 | 2d | 92 | |
5 | 4-OCF3C6H4 | 25 | 2e | 65 | |
6 | 4-ClC6H4 | 20 | 2f | 48 | |
7 | 3-ClC6H4 | 20 | 2g | 63 | |
8 | 3-BrC6H4 | 30 | 2h | 62 | |
9 | 2-CH3COC6H4 | 50 | 2i | 63 | |
10 | 4-CH3OOCC6H4 | 23 | 2j | 60 | |
11 | 3-CNC6H4 | 39 | 2k | 68 | |
12 | 3-NO2C6H4 | 30 | 2l | 54 | |
13 | 2-thiophenyl | 25 | 2m | 65 | |
14 | 2-thiazolyl | 24 | 2n | 51 | |
15 | 3-pyridyl | 20 | 2o | 60 | |
16 | 1p | - | 30 | 2p | 62 |
17 | 1q | - | 40 | 2q | trace |
18 | 1r | - | 10 | 2r | 66 |
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Zeng, M.; Chen, J.-L.; Luo, X.; Zou, Y.-J.; Liu, Z.-N.; Dai, J.; Jiang, D.-Z.; Li, J.-J. Oxygen-Free Csp3-H Oxidation of Pyridin-2-yl-methanes to Pyridin-2-yl-methanones with Water by Copper Catalysis. Molecules 2023, 28, 7587. https://doi.org/10.3390/molecules28227587
Zeng M, Chen J-L, Luo X, Zou Y-J, Liu Z-N, Dai J, Jiang D-Z, Li J-J. Oxygen-Free Csp3-H Oxidation of Pyridin-2-yl-methanes to Pyridin-2-yl-methanones with Water by Copper Catalysis. Molecules. 2023; 28(22):7587. https://doi.org/10.3390/molecules28227587
Chicago/Turabian StyleZeng, Ming, Jia-Le Chen, Xue Luo, Yan-Jiao Zou, Zhao-Ning Liu, Jun Dai, Deng-Zhao Jiang, and Jin-Jing Li. 2023. "Oxygen-Free Csp3-H Oxidation of Pyridin-2-yl-methanes to Pyridin-2-yl-methanones with Water by Copper Catalysis" Molecules 28, no. 22: 7587. https://doi.org/10.3390/molecules28227587