PEG1000-Based Dicationic Acidic Ionic Liquid/Solvent-Free Conditions: An Efficient Catalytic System for the Synthesis of Bis(Indolyl)methanes
Abstract
:1. Introduction
2. Results and Discussion
2.1. Effects of Different Reaction Conditions
2.2. Effects of Different Substrates
2.3. Effects of Different Catalysts
3. Experimental Section
3.1. Materials and Methods
3.2. Typical Procedure for the Synthesis of Bis(indolyl)methanes
4. Conclusions
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Entry | PEG1000-DAIL (mol %) | t (min) | Yield (%) a |
---|---|---|---|
1 | 0 | 20 | trace |
2 | 1 | 20 | 75 |
3 | 2 | 12 | 85 |
4 b | 3 | 3 | 98, 98, 97, 97, 95, 94, 90 |
5 | 4 | 3 | 98 |
6 | 5 | 3 | 98 |
Entry | R1 | R2 | R3 | R4 | t (min) | Product | Yield (%) a |
---|---|---|---|---|---|---|---|
1 | C6H5 | H | H | H | 3 | 3a | 98 |
2 | 4-ClC6H4 | H | H | H | 2 | 3b | 98 |
3 | 2-ClC6H4 | H | H | H | 2 | 3c | 98 |
4 | 4-CH3C6H4 | H | H | H | 10 | 3d | 96 |
5 | 4-CH3OC6H4 | H | H | H | 10 | 3e | 95 |
6 | 2-CH3OC6H4 | H | H | H | 8 | 3f | 93 |
7 | 4-NO2C6H4 | H | H | H | 2 | 3g | 98 |
8 | 3-NO2C6H4 | H | H | H | 3 | 3h | 94 |
9 | 4-BrC6H4 | H | H | H | 2 | 3i | 95 |
10 | 4-HOC6H4 | H | H | H | 10 | 3j | 96 |
11 | C6H5 | H | CH3 | H | 3 | 3k | 94 |
12 | 4-ClC6H4 | H | CH3 | H | 2 | 3l | 96 |
13 | 4-CH3C6H4 | H | CH3 | H | 10 | 3m | 95 |
14 | 3-NO2C6H4 | H | CH3 | H | 3 | 3n | 95 |
15 | 4-NO2C6H4 | H | CH3 | H | 2 | 3o | 97 |
16 | C6H5 | H | H | CH3 | 4 | 3p | 96 |
17 | 4-NO2C6H4 | H | H | CH3 | 3 | 3q | 98 |
18 | 4-CH3C6H4 | H | H | CH3 | 10 | 3r | 96 |
19 | CH3(CH2)3 | H | H | H | 15 | 3s | 92 |
20 | C6H5CH=CH | H | H | H | 5 | 3t | 95 |
21 | C6H5 | CH3 | H | H | 25 | 3u | 95 |
22 | 4-NO2C6H4 | CH3 | H | H | 18 | 3v | 97 |
23 | CH3 | CH3 | H | H | 50 | 3w | 73 |
24 | (CH2)5 | H | H | 40 | 3x | 81 |
Entry | Catalysts | Amount (mmol) | Solvents | T (°C) | t (h) | Yield (%) |
---|---|---|---|---|---|---|
1 | PEG1000-DAIL | 0.03 | No | r.t. | 0.05 | 98 |
2 | Ascorbic Acid | 0.14 | EtOH | r.t. | 0.5 | 89 [7] |
3 | Sulfated Zirconia | 0.30 | No | r.t. | 24 | 97 [29] |
4 | BF3∙Et2O | 0.15 | Et2O | r.t. | 2 | 90 [30] |
5 | Bu4NBr3 | 0.08 | EtOH | r.t. | 2.5 | 72 [31] |
6 | Cyclic phosphoric acid | 0.01 | CH2Cl2 | r.t. | 2.5 | 97 [32] |
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Ren, Y.-M.; Xu, M.-D.; Wang, X. PEG1000-Based Dicationic Acidic Ionic Liquid/Solvent-Free Conditions: An Efficient Catalytic System for the Synthesis of Bis(Indolyl)methanes. Catalysts 2017, 7, 300. https://doi.org/10.3390/catal7100300
Ren Y-M, Xu M-D, Wang X. PEG1000-Based Dicationic Acidic Ionic Liquid/Solvent-Free Conditions: An Efficient Catalytic System for the Synthesis of Bis(Indolyl)methanes. Catalysts. 2017; 7(10):300. https://doi.org/10.3390/catal7100300
Chicago/Turabian StyleRen, Yi-Ming, Mao-Dong Xu, and Xiong Wang. 2017. "PEG1000-Based Dicationic Acidic Ionic Liquid/Solvent-Free Conditions: An Efficient Catalytic System for the Synthesis of Bis(Indolyl)methanes" Catalysts 7, no. 10: 300. https://doi.org/10.3390/catal7100300