Synthesis of New 2-Arylbenzo[b]furan Derivatives via Palladium-Catalyzed Suzuki Cross-Coupling Reactions in Aqueous Media
Abstract
:1. Introduction
2. Results and Discussion
3. Experimental
3.1. General Information
3.2. General Procedure for Suzuki Coupling
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
References
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Sample Availability: Samples of the compounds are not available from the authors. |
Entry | Catalyst | Loading of Catalyst (mol%) | Base (mmol) | Solvent (mL) (1:1) | Temperature (°C) | Time (h) | Yield b (%) |
---|---|---|---|---|---|---|---|
1 | PdCl2 | 2 | K2CO3 | EtOH + H2O | 80 | 4 | 55 |
2 | Pd(OAc)2 | 2 | K2CO3 | EtOH + H2O | 80 | 4 | 61 |
3 | Pd(II) (10) | 2 | K2CO3 | EtOH + H2O | 80 | 4 | 91 |
4 | Pd(II) (10) | 1 | K2CO3 | EtOH + H2O | 80 | 4 | 62 |
5 | Pd(II) (10) | 3 | K2CO3 | EtOH + H2O | 80 | 4 | 97 |
6 | Pd(II) (10) | 4 | K2CO3 | EtOH + H2O | 80 | 4 | 95 |
7 | Pd(II) (10) | 3 | NEt3 | EtOH + H2O | 80 | 4 | 28 |
8 | Pd(II) (10) | 3 | NaF | EtOH + H2O | 80 | 4 | 40 |
9 | Pd(II) (10) | 3 | KHCO3 | EtOH + H2O | 80 | 4 | 53 |
10 | Pd(II) (10) | 3 | NaOH | EtOH + H2O | 80 | 4 | 78 |
11 | Pd(II) (10) | 3 | Cs2CO3 | EtOH + H2O | 80 | 4 | 63 |
12 | Pd(II) (10) | 3 | K2CO3 | EtOH | 80 | 4 | 32 |
13 | Pd(II) (10) | 3 | K2CO3 | H2O | 80 | 4 | 0 |
14 | Pd(II) (10) | 3 | K2CO3 | DMSO | 80 | 4 | 0 |
15 | Pd(II) (10) | 3 | K2CO3 | DMF | 80 | 4 | trace |
16 | Pd(II) (10) | 3 | K2CO3 | EtOH + H2O | 40 | 4 | 13 |
17 | Pd(II) (10) | 3 | K2CO3 | EtOH + H2O | 60 | 4 | 47 |
18 | Pd(II) (10) | 3 | K2CO3 | EtOH + H2O | 80 | 1 | 71 |
19 | Pd(II) (10) | 3 | K2CO3 | EtOH + H2O | 80 | 2 | 93 |
20 | Pd(II) (10) | 3 | K2CO3 | EtOH + H2O | 80 | 3 | 95 |
21 | Pd(II) (10) | 3 | K2CO3 | EtOH + H2O | 80 | 5 | 98 |
Entry | Arylboronic Acid (8) | Product (9) | Yield b (%) |
---|---|---|---|
1 | 8a | 9a | 97 |
2 | 8b | 9b | 97 |
3 | 8c | 9c | 92 |
4 | 8d | 9d | 95 |
5 | 8e | 9e | 85 |
6 | 8f | 9f | 78 |
7 | 8g | 9g | 96 |
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Chen, Q.; Jiang, P.; Guo, M.; Yang, J. Synthesis of New 2-Arylbenzo[b]furan Derivatives via Palladium-Catalyzed Suzuki Cross-Coupling Reactions in Aqueous Media. Molecules 2018, 23, 2450. https://doi.org/10.3390/molecules23102450
Chen Q, Jiang P, Guo M, Yang J. Synthesis of New 2-Arylbenzo[b]furan Derivatives via Palladium-Catalyzed Suzuki Cross-Coupling Reactions in Aqueous Media. Molecules. 2018; 23(10):2450. https://doi.org/10.3390/molecules23102450
Chicago/Turabian StyleChen, Qianqian, Panli Jiang, Mengping Guo, and Jianxin Yang. 2018. "Synthesis of New 2-Arylbenzo[b]furan Derivatives via Palladium-Catalyzed Suzuki Cross-Coupling Reactions in Aqueous Media" Molecules 23, no. 10: 2450. https://doi.org/10.3390/molecules23102450