Reactivity of Aryl Halides for Reductive Dehalogenation in (Sea)water Using Polymer-Supported Terpyridine Palladium Catalyst
Abstract
:1. Introduction
2. Results and Discussion
Run | R1:2 | R1:3 | Yield (%) (Water) | Yield (%) (Seawater) | Yield (%) (Seawater) |
---|---|---|---|---|---|
1 | p-Ac:2a | Ac:3a | 94 | 56 | 94 c |
2 | m-Ac:2b | 3a | 96 | 65 | 95 c |
3 | o-Ac:2c | 3a | 95 | 44 | 91 c |
4 b | p-B:2d | Bz:3b | 94 | 52 | 87 c |
5 b | m-Bz:2e | 3b | 94 | 84 | 84 c |
6 b | o-Bz:2f | 3b | 93 | 68 | 68 c |
7 b | p-NH2:2g | NH2:3c | 93 | 9 | 94 c |
8 | m-NH2:2h | 3c | 95 | 44 | 95 c |
9 | o-NH2:2i | 3c | 96 | 33 | 95 c |
10 | p-OH:2j | OH:3d | 94 | 90 | 94 c |
11 | m-OH:2k | 3d | 94 | 77 | 94 c |
12 | o-OH:2l | 3d | 94 | 59 | 94 c |
13 | Ac, 2,5-Cl:2m | 3a | 90 | 21 | 58 c |
14 d | Ac, 2,3,5-Cl:2n | 3a | 96 e | 43 | 90 e |
Run | Salts | Amount of Salts (mol) 100 ppm | Yield (%) a |
---|---|---|---|
1 | none | --- | 94 |
2 | NaF | 3.57 × 10−6 | 94 |
3 | NaCl | 2.57 × 10−6 | 95 |
4 | NaBr | 1.46 × 10−6 | 63 |
5 | NaI | 1.00 × 10−6 | 60 |
6 | Na2SO4·10H2O | 0.47 × 10−6 | 96 |
7 | Na2CO3 | 1.42 × 10−6 | 95 |
8 | NaH2PO4·2H2O | 0.96 × 10−6 | 95 |
9 | AgNO3 | 1.59 × 10−6 | 92 |
10 | AgNO3, NaBr | 1.50 × 10−6 | 96 |
11 b | AgNO3 | 1.59 × 10−6 | 0 |
12 b,c | None | --- | 94 |
Entry | Aryl Halide | Yield (%) a |
---|---|---|
1 | 4-Cl-acetophenone 2a | quant. |
2 b | 4-Br-acetophenone 2o | 74 |
3 b | 4-I-acetophenone 2p | 0.5 |
3. Experimental Section
3.1. General Methods
3.2. Materials
3.3. Synthesis of Polymer-Supported Ligand
3.4. Preparation of PS–PEG Resin-Supported Terpyridine Palladium Complex 1
3.5. Hydrodechlorination of Aryl Chlorides
4. Conclusions
Acknowledgments
Author Contributions
Conflicts of Interest
References and Notes
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Suzuka, T.; Sueyoshi, H.; Maehara, S.; Ogasawara, H. Reactivity of Aryl Halides for Reductive Dehalogenation in (Sea)water Using Polymer-Supported Terpyridine Palladium Catalyst. Molecules 2015, 20, 9906-9914. https://doi.org/10.3390/molecules20069906
Suzuka T, Sueyoshi H, Maehara S, Ogasawara H. Reactivity of Aryl Halides for Reductive Dehalogenation in (Sea)water Using Polymer-Supported Terpyridine Palladium Catalyst. Molecules. 2015; 20(6):9906-9914. https://doi.org/10.3390/molecules20069906
Chicago/Turabian StyleSuzuka, Toshimasa, Hiromu Sueyoshi, Shohei Maehara, and Hiroaki Ogasawara. 2015. "Reactivity of Aryl Halides for Reductive Dehalogenation in (Sea)water Using Polymer-Supported Terpyridine Palladium Catalyst" Molecules 20, no. 6: 9906-9914. https://doi.org/10.3390/molecules20069906
APA StyleSuzuka, T., Sueyoshi, H., Maehara, S., & Ogasawara, H. (2015). Reactivity of Aryl Halides for Reductive Dehalogenation in (Sea)water Using Polymer-Supported Terpyridine Palladium Catalyst. Molecules, 20(6), 9906-9914. https://doi.org/10.3390/molecules20069906