pH-Dependence of the Aqueous Phase Room Temperature Brønsted Acid-Catalyzed Chemoselective Oxidation of Sulfides with H2O2
Abstract
:1. Introduction
2. Results and Discussion
Entry | Catalyst Loading (%) | Conversion (%) b | Yield (%) b |
---|---|---|---|
1 | 0.0 | 34.1 | 34.1 |
2 | 2.5 | 41.6 | 41.5 |
3 | 5.0 | 51.8 | 51.5 |
4 | 7.5 | 56.2 | 56.0 |
5 | 10.0 | 59.5 | 59.2 |
6 | 12.5 | 64.4 | 64.0 |
7 | 15.0 | 79.4 | 78.8 |
8 | 17.5 | 84.5 | 83.9 |
9 | 20.0 | 93.4 | 92.7 |
10 | 22.5 | 97.6 | 96.8 |
11 | 25.0 | 99.2 | 98.3 |
Entry | Brønsted Acid | Amount (mmol) | pH Value b | Conversion (%) c | Yield (%) c |
---|---|---|---|---|---|
1 | 0.25 | 1.28 | 99.6 | 99.3 | |
2 | CH3SO3H | 0.25 | 1.25 | 99.7 | 98.8 |
3 | 0.25 | 1.30 | 99.7 | 98.8 | |
4 | HCOOH | 4.00 | 1.31 | 99.1 | 98.6 |
5 | CH3COOH | 5.50 | 1.35 | 99.1 | 98.9 |
Entry | pH Value b | Conversion (%) c | Yield (%) c |
---|---|---|---|
1 | 2.00 | 42.6 | 42.6 |
2 | 1.90 | 49.5 | 49.2 |
3 | 1.80 | 58.1 | 57.9 |
4 | 1.70 | 66.9 | 66.4 |
5 | 1.60 | 72.1 | 71.4 |
6 | 1.50 | 77.9 | 77.1 |
7 | 1.40 | 98.1 | 96.3 |
8 | 1.30 | 99.6 | 98.9 |
9 | 1.20 | 99.8 | 98.6 |
10 | 1.10 | 99.6 | 97.2 |
11 | 1.00 | 99.4 | 96.5 |
Entry | Brønsted Acid | Conversion (%) c | Yield (%) c |
---|---|---|---|
1 | 99.6 | 98.9 | |
2 | CH3SO3H | 99.8 | 98.7 |
3 | 99.7 | 98.5 | |
4 | 98.7 | 97.9 | |
5 | HCOOH | 99.6 | 99.1 |
6 | CH3COOH | 99.2 | 98.6 |
7 | HOOCCOOH | 99.7 | 98.3 |
8 | 99.8 | 98.5 | |
9 | CF3COOH | 98.8 | 97.7 |
10 | H2SO4 | 99.6 | 99.1 |
11 | HCL | 99.7 | 98.8 |
12 | H3PO4 | 99.5 | 98.9 |
13 | H3BO3 | 99.6 | 98.7 |
14 | 99.6 | 98.8 | |
15 | 99.7 | 98.5 |
Entry | Sulfide | Conversion (%) c | Yield (%) c |
---|---|---|---|
1 | 99.6 | 98.9 | |
2 | 98.7 | 97.9 | |
3 | 99.9 | 99.4 | |
4 | 99.4 | 98.8 | |
5 d | 98.5 | 97.6 | |
6 d | 98.1 | 97.4 | |
7 d | 98.7 | 98.2 | |
8 | 99.5 | 99.1 | |
9 | 99.9 | 99.4 | |
10 d | 98.7 | 97.9 | |
11 d | 96.8 | 95.6 | |
12 | 99.2 | 98.6 |
3. Experimental Section
3.1. General Information
3.2. Materials
3.3. General Procedure for Oxidation of Sulfides Catalyzed by Brønsted Acid (1)
3.4. General Procedure for Oxidation of Sulfides Catalyzed by Brønsted Acid (2)
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Shen, H.-M.; Zhou, W.-J.; Ma, X.; Wu, H.-K.; Yu, W.-B.; Ai, N.; Ji, H.-B.; Shi, H.-X.; She, Y.-B. pH-Dependence of the Aqueous Phase Room Temperature Brønsted Acid-Catalyzed Chemoselective Oxidation of Sulfides with H2O2. Molecules 2015, 20, 16709-16722. https://doi.org/10.3390/molecules200916709
Shen H-M, Zhou W-J, Ma X, Wu H-K, Yu W-B, Ai N, Ji H-B, Shi H-X, She Y-B. pH-Dependence of the Aqueous Phase Room Temperature Brønsted Acid-Catalyzed Chemoselective Oxidation of Sulfides with H2O2. Molecules. 2015; 20(9):16709-16722. https://doi.org/10.3390/molecules200916709
Chicago/Turabian StyleShen, Hai-Min, Wen-Jie Zhou, Xin Ma, Hong-Ke Wu, Wu-Bin Yu, Ning Ai, Hong-Bing Ji, Hong-Xin Shi, and Yuan-Bin She. 2015. "pH-Dependence of the Aqueous Phase Room Temperature Brønsted Acid-Catalyzed Chemoselective Oxidation of Sulfides with H2O2" Molecules 20, no. 9: 16709-16722. https://doi.org/10.3390/molecules200916709