Aqueous Synthesis of 1-H-2-Substituted Benzimidazoles via Transition-Metal-Free Intramolecular Amination of Aryl Iodides
Abstract
:1. Introduction
2. Results and Discussion
Entry | Substrate | Base | Temperature (°C) | Time (h) | Yield (%) [b] |
---|---|---|---|---|---|
1 | 1a | ― | 100 | 30 | 0 |
2 | 1a | K2CO3 | 100 | 30 | 80 |
3 | 1a | KOH | 100 | 30 | 63 |
4 | 1a | K3PO4 | 100 | 30 | trace |
5 | 1a | NaOH | 100 | 30 | 0 |
6 | 1a | NaHCO3 | 100 | 30 | 0 |
7 | 1a | Na2CO3 | 100 | 30 | 0 |
8 | 1a | Cs2CO3 | 100 | 30 | 84 |
9 | 1a | Et3N | 100 | 30 | 0 |
10 | 1a | Pyridine | 100 | 30 | 0 |
11 [c] | 1a | K2CO3 | 80 | 30 | trace |
12 | 1a | K2CO3 | 90 | 30 | 60 |
13 | 1a | K2CO3 | 100 | 20 | 50 |
14 | 1a | K2CO3 | 100 | 48 | 74 |
15 [d] | 1a | K2CO3 | 120 | 30 | 78 |
16 [d] | 1a | K2CO3 | 150 | 30 | 66 |
17 | 1a' | K2CO3 | 100 | 30 | 0 |
18 | 1a'' | K2CO3 | 100 | 30 | 0 |
Entry | Substrate | Product | Yield (%) [b] |
---|---|---|---|
1 | 1a | 2a | 80 |
2 | 1b | 2b | 77 |
3c | 1b' | 2b | 0 |
4 | 1c | 2c | 66 |
5 | 1d | 2d | 54 |
6 | 1e | 2e | 67 |
7 | 1f | 2f | 67 |
8 | 1g | 2g | 44 |
9 [c] | 1g' | 2g | 0 |
10 [c] | 1h | 2h | 0 |
Entry | Substrate | Product | Yield (%) [b] |
---|---|---|---|
1 | 1i | 2i | 60 |
2 | 1j | 2j | 63 |
3 | 1k | 2k | 58 |
4 | 1l | 2l | 64 |
5 | 1m | 2m | 70 |
6 | 1n | 2n | 50 |
7 [c] | 1o | 2o | 0 |
8 [c] | 1p | 2p | 0 |
9 | 1q | 2q | 48 |
10 | 1r | 2r | 60 |
11 | 1s | 2s | 48 |
12 [c] | 1t | 2t | 0 |
13 | 1u | 2u | 33 |
3. Experimental
3.1. General
3.2. Chemistry
3.2.1. General Procedure for the Preparation of Benzimidazoles 2a–u
4. Conclusions
Acknowledgments
References and Notes
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Chen, C.; Chen, C.; Li, B.; Tao, J.; Peng, J. Aqueous Synthesis of 1-H-2-Substituted Benzimidazoles via Transition-Metal-Free Intramolecular Amination of Aryl Iodides. Molecules 2012, 17, 12506-12520. https://doi.org/10.3390/molecules171112506
Chen C, Chen C, Li B, Tao J, Peng J. Aqueous Synthesis of 1-H-2-Substituted Benzimidazoles via Transition-Metal-Free Intramolecular Amination of Aryl Iodides. Molecules. 2012; 17(11):12506-12520. https://doi.org/10.3390/molecules171112506
Chicago/Turabian StyleChen, Chunxia, Chen Chen, Bin Li, Jingwei Tao, and Jinsong Peng. 2012. "Aqueous Synthesis of 1-H-2-Substituted Benzimidazoles via Transition-Metal-Free Intramolecular Amination of Aryl Iodides" Molecules 17, no. 11: 12506-12520. https://doi.org/10.3390/molecules171112506