Palladium on Carbon-Catalyzed Suzuki-Miyaura Coupling Reaction Using an Efficient and Continuous Flow System
Abstract
:1. Introduction
2. Results and Discussion
Entry | Flow rate (mL/min) | Temperature (°C) | Na2CO3 (equiv) | 1H NMR ratio |
---|---|---|---|---|
1:2 | ||||
1 | 1 | 25 | 1.5 | 0:100 (100) a |
2 | 2 | 25 | 1.5 | 21:79 |
3 | 2 | 100 | 1.5 | 0:100 |
4 | 3 | 25 | 1.5 | 32:68 |
5 | 3 | 100 | 1.5 | 6:94 |
6 | 1 | 25 | 1.2 | 56:44 |
7 | 1 | 25 | 1.0 | 100:0 |
Entry | X | R1 | R2 | Temperature (°C) | Yield (%) a |
---|---|---|---|---|---|
1 [9] | I | 4-Ac | H | 25 | 100 |
2 [16] | I | 4-CO2Et | H | 25 | 92 |
3 [18] | I | 2-CO2Et | H | 75 | 88 |
4 [9] | I | 4-Me | H | 75 | 91 |
5 [16] | I | 4-OMe | H | 75 | 81 |
6 [19] | I | 4-Ac | 3-Ac | 25 | 99 |
7 [18] | I | 4-CO2Et | 4-Ac | 25 | 91 |
8 [9] | I | 4-OMe | 4-Ac | 75 | 97 |
9 [9] | I | 4-Ac | 4-OMe | 50 | 89 |
10 [18] | I | 4-CO2Et | 4-OMe | 75 | 97 |
11 [20] | I | 4-Me | 4-OMe | 75 | 100 |
12 [21] | I | 3-Me | 4-OMe | 75 | 98 |
13 [21] | I | 2-Me | 4-OMe | 75 | 98 |
14 [22] | I | 4-OMe | 2,4-di-OMe | 100 | 78 |
15 [9] | Br | 4-Ac | H | 50 | 90 |
16 [16] | Br | 4-CO2Et | H | 100 | 78 |
17 [9] | Br | 4-Ac | 4-OMe | 50 | 97 |
18 [18] | Br | 4-CO2Et | 4-OMe | 75 | 100 |
Entry | Layer | 1H NMR ratio | Pd leaching |
---|---|---|---|
1:2 | |||
1 | Organic | 0:100 (99) a | <1 ppm |
2 | Aquous | <1 ppm |
3. Experimental Section
3.1. General Procedure
3.2. Typical Procedure for the Palladium on Carbon-Catalyzed Cross-Coupling Reaction under Flow Conditions
3.3. Leaching Test of Palladium (Table 3)
4. Conclusions
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Hattori, T.; Tsubone, A.; Sawama, Y.; Monguchi, Y.; Sajiki, H. Palladium on Carbon-Catalyzed Suzuki-Miyaura Coupling Reaction Using an Efficient and Continuous Flow System. Catalysts 2015, 5, 18-25. https://doi.org/10.3390/catal5010018
Hattori T, Tsubone A, Sawama Y, Monguchi Y, Sajiki H. Palladium on Carbon-Catalyzed Suzuki-Miyaura Coupling Reaction Using an Efficient and Continuous Flow System. Catalysts. 2015; 5(1):18-25. https://doi.org/10.3390/catal5010018
Chicago/Turabian StyleHattori, Tomohiro, Aya Tsubone, Yoshinari Sawama, Yasunari Monguchi, and Hironao Sajiki. 2015. "Palladium on Carbon-Catalyzed Suzuki-Miyaura Coupling Reaction Using an Efficient and Continuous Flow System" Catalysts 5, no. 1: 18-25. https://doi.org/10.3390/catal5010018