Microwave Assisted Suzuki-Miyaura and Ullmann Type Homocoupling Reactions of 2- and 3-Halopyridines Using a Pd(OAc)2/Benzimidazolium Salt and Base Catalyst System
Abstract
:1. Introduction
2. Results and Discussion
2.1. The Suzuki-Miyaura Type Coupling Reaction
Entry | X | Y | Z | Salt | % Yields | ||||
---|---|---|---|---|---|---|---|---|---|
1 a | Br | N | CH | - | 40.3 | 13.8 | 1.1 | 0.6 | 17.2 |
2 b | Br | N | CH | 2 | 2.0 | - | - | - | - |
3 c | Br | N | CH | 2 | 57.6 | 5.3 | - | - | 15.6 |
4 d | Br | N | CH | 2 | 63.4 | 4.7 | 0.8 | - | 7.1 |
5 e | Br | N | CH | 2 | 70.0 | 22.0 | 0.3 | 0.7 | 7.0 |
6 | Br | N | CH | I | 65.0 | 23.7 | 0.7 | 0.7 | 9.9 |
7 | Br | N | CH | 1 | 67.0 | 27.2 | - | 1.6 | 4.2 |
8 | Br | N | CH | 3 | 72.5 | 17.8 | 0.6 | 1.3 | 7.8 |
9 | Br | N | CH | 4 | 66.8 | 18.8 | - | - | 4.4 |
10 | Cl | N | CH | I | 61.9 | 12.0 | 0.4 | 3.1 | 12.6 |
11 | Cl | N | CH | 1 | 64.1 | 14.5 | - | 9.1 | 6.1 |
12 | Cl | N | CH | 2 | 65.4 | 12.4 | 0.2 | 5.4 | 12.8 |
13 | Cl | N | CH | 3 | 66.1 | 12.5 | - | 4.4 | 9.0 |
14 | Cl | N | CH | 4 | 51.8 | 2.5 | - | 6.8 | 4.3 |
15 | Br | CH | N | I | 90.0 | - | - | 2.8 | 7.2 |
16 | Br | CH | N | 1 | 89.3 | - | - | 2.1 | 8.6 |
17 | Br | CH | N | 2 | 91.2 | - | - | 2.9 | 5.9 |
18 | Br | CH | N | 3 | 93.4 | 0.7 | - | 1.9 | 4.0 |
19 | Br | CH | N | 4 | 90.0 | - | - | 2.4 | 7.6 |
20 | Cl | CH | N | I | 66.6 | - | - | 2.5 | 23.8 |
21 | Cl | CH | N | 1 | 76.5 | - | - | 6.7 | 12.5 |
22 | Cl | CH | N | 2 | 70.1 | 0.7 | - | 2.0 | 16.4 |
23 | Cl | CH | N | 3 | 73.5 | - | - | 1.8 | 18.5 |
24 | Cl | CH | N | 4 | 58.0 | - | - | 4.8 | 9.2 |
2.2. The Ullmann Type Homocoupling Reaction
Entry | X | Y | Z | Salt | % Yields | ||
---|---|---|---|---|---|---|---|
1 a | Br | N | CH | 2 | 1.3 | - | - |
2 b | Br | N | CH | 2 | 12.0 | - | 0.4 |
3 c | Br | N | CH | 2 | 43.5 | 9.9 | - |
4 d | Br | N | CH | 2 | 48.5 | 2.5 | - |
5 | Br | N | CH | I | 84.5 | 2.4 | 12.9 |
6 | Br | N | CH | 1 | 75.1 | 8.3 | 16.6 |
7 | Br | N | CH | 2 | 69.7 | 12.2 | 1.8 |
8 | Br | N | CH | 3 | 74.4 | 14.3 | 3.8 |
9 | Br | N | CH | 4 | 33.7 | 9.8 | 3.6 |
10 | Cl | N | CH | I | 64.3 | 0.6 | 34.4 |
11 | Cl | N | CH | 1 | 31.4 | 3.4 | 47.7 |
12 | Cl | N | CH | 2 | 46.5 | 5.1 | 23.2 |
13 | Cl | N | CH | 3 | 20.9 | 5.5 | 15.2 |
14 | Cl | N | CH | 4 | 8.0 | 5.5 | 3.7 |
15 | Br | CH | N | I | 15.0 | - | 85.0 |
16 | Br | CH | N | 1 | 5.2 | - | 94.8 |
17 | Br | CH | N | 2 | 6.6 | - | 93.4 |
18 | Br | CH | N | 3 | 2.3 | - | 97.7 |
19 | Br | CH | N | 4 | - | - | 62.2 |
20 | Cl | CH | N | I | 1.0 | - | 26.1 |
21 | Cl | CH | N | 1 | - | - | 40.6 |
22 | Cl | CH | N | 2 | 1.6 | - | 11.4 |
23 | Cl | CH | N | 3 | 1.0 | - | 10.6 |
24 | Cl | CH | N | 4 | - | - | 21.6 |
3. Experimental
3.1. General Procedures
3.2. General Procedure for the Suzuki-Miyaura and the Ullmann Type Homocoupling Reactions
3.2.1. The Suzuki-Miyaura Reaction
3.2.2. Ullmann Type Homocoupling Reaction
4. Conclusions
Supplementary Materials
Acknowledgments
References
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Yılmaz, Ü.; Deniz, S.; Küçükbay, H.; Şireci, N. Microwave Assisted Suzuki-Miyaura and Ullmann Type Homocoupling Reactions of 2- and 3-Halopyridines Using a Pd(OAc)2/Benzimidazolium Salt and Base Catalyst System. Molecules 2013, 18, 3712-3724. https://doi.org/10.3390/molecules18043712
Yılmaz Ü, Deniz S, Küçükbay H, Şireci N. Microwave Assisted Suzuki-Miyaura and Ullmann Type Homocoupling Reactions of 2- and 3-Halopyridines Using a Pd(OAc)2/Benzimidazolium Salt and Base Catalyst System. Molecules. 2013; 18(4):3712-3724. https://doi.org/10.3390/molecules18043712
Chicago/Turabian StyleYılmaz, Ülkü, Selma Deniz, Hasan Küçükbay, and Nihat Şireci. 2013. "Microwave Assisted Suzuki-Miyaura and Ullmann Type Homocoupling Reactions of 2- and 3-Halopyridines Using a Pd(OAc)2/Benzimidazolium Salt and Base Catalyst System" Molecules 18, no. 4: 3712-3724. https://doi.org/10.3390/molecules18043712