Geometry Constrained N-(5,6,7-Trihydroquinolin-8-ylidene)arylaminopalladium Dichloride Complexes: Catalytic Behavior toward Methyl Acrylate (MA), Methyl Acrylate-co-Norbornene (MA-co-NB) Polymerization and Heck Coupling
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis and Characterization of Palladium Complexes
2.2. Single Crystal X-ray Diffraction Study
2.3. Polymerization of MA and Copolymerization of MA/NB
2.4. Heck Coupling Reaction
3. Experimental Section
3.1. General Information
3.2. Synthesis of Ligands L1–L5
3.3. Synthesis of Palladium Complexes
3.4. Homopolymerization of MA
3.5. Copolymerization of MA and NB
3.6. Heck Reaction
3.7. X-ray Crystallographic Study
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Run | Pre-Catalyst | T (°C) | Time (h) | Yield (g) | Conversion (%) b | Mw c (kg∙mol−1) | Mw/Mn c |
---|---|---|---|---|---|---|---|
1 | Pd3 | 80 | 4 | 7.30 | 77.0 | 1498 | 2.33 |
2 | Pd3 | 100 | 4 | 9.01 | 95.0 | 2252 | 11.5 |
3 | Pd3 | 120 | 4 | 6.01 | 63.4 | 1091 | 1.74 |
4 | Pd3 | 100 | 1 | 2.21 | 24.2 | 1534 | 3.54 |
5 | Pd3 | 100 | 2 | 5.22 | 56.1 | 1734 | 2.39 |
6 | Pd3 | 100 | 3 | 7.44 | 79.4 | 1830 | 3.46 |
7 | Pd1 | 100 | 4 | 7.70 | 82.0 | 1936 | 3.21 |
8 | Pd2 | 100 | 4 | 8.76 | 93.4 | 1163 | 3.79 |
9 | Pd4 | 100 | 4 | 9.15 | 97.2 | 1596 | 3.98 |
10 | Pd5 | 100 | 4 | 9.28 | 98.4 | 6282 | 3.73 |
11 d | Pd3 | 100 | 4 | - | - | - | - |
Run a | MA/NBE | Yield (g) | Conversion of MA (%) b | NB/MA b | Mw c/kg∙mol−1 | Mw/Mn c |
---|---|---|---|---|---|---|
1 | 1:0 | 9.01 | 95 | - | 2252 | 1.74 |
2 | 9:1 | 7.38 | 68 | 8 | 1699 | 2.69 |
3 | 7:3 | 5.21 | 49 | 16 | 202 | 5.74 |
4 | 5:5 | 3.49 | 30 | 18 | 152 | 4.59 |
5 | 0:1 | - | - | - | - | - |
Run | Catalyst | Base | T (°C) | Solvent | Time (h) | Conversion (%) b | ToF c |
---|---|---|---|---|---|---|---|
1 | Pd5 | K2CO3 | 150 | DMA | 8 | 93 | 5813 |
2 | Pd5 | Na2CO3 | 150 | DMA | 8 | 72 | 4500 |
3 | Pd5 | NaHCO3 | 150 | DMA | 8 | 74 | 4625 |
4 | Pd5 | NaOAc | 150 | DMA | 8 | 82 | 5125 |
5 | Pd5 | NaOH | 150 | DMA | 8 | 70 | 4375 |
6 | Pd5 | K2CO3 | 150 | DMF | 8 | 92 | 5750 |
7 | Pd5 | K2CO3 | 100 | Toluene | 8 | - | - |
8 | Pd5 | K2CO3 | 60 | CH3CN | 8 | - | - |
9 | Pd5 | K2CO3 | 100 | DMA | 8 | - | - |
10 | Pd5 | K2CO3 | 60 | DMA | 8 | - | - |
11 | Pd5 | K2CO3 | 150 | DMA | 2 | 86 | 21500 |
12 | Pd5 | K2CO3 | 150 | DMA | 4 | 88 | 11000 |
13 | Pd5 | K2CO3 | 150 | DMA | 12 | 98 | 4083 |
14 | Pd4 | K2CO3 | 150 | DMA | 08 | 93 | 5813 |
15 d | PdCl2 | K2CO3 | 150 | DMA | 08 | 22 | 28 |
16 d | Pd(OAc)2 | K2CO3 | 150 | DMA | 08 | 41 | 50 |
Run | Ar–X | Yield (%) b | Conversion (%) c | ToF d |
---|---|---|---|---|
1 | | 74 | 81 | 3905 |
2 | | - | 3.6 | 225 |
3 | | 31 (15) | 43 (21) | 1938 (938) |
4 | | 64 | 77 | 4000 |
5 | | 65 | 76 | 3847 |
6 | | 37 | 53 | 2312 |
7 | | - | 6 | 375 |
8 | | - | 8 | 500 |
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Zeng, Y.; Mahmood, Q.; Liang, T.; Sun, W.-H. Geometry Constrained N-(5,6,7-Trihydroquinolin-8-ylidene)arylaminopalladium Dichloride Complexes: Catalytic Behavior toward Methyl Acrylate (MA), Methyl Acrylate-co-Norbornene (MA-co-NB) Polymerization and Heck Coupling. Molecules 2016, 21, 1686. https://doi.org/10.3390/molecules21121686
Zeng Y, Mahmood Q, Liang T, Sun W-H. Geometry Constrained N-(5,6,7-Trihydroquinolin-8-ylidene)arylaminopalladium Dichloride Complexes: Catalytic Behavior toward Methyl Acrylate (MA), Methyl Acrylate-co-Norbornene (MA-co-NB) Polymerization and Heck Coupling. Molecules. 2016; 21(12):1686. https://doi.org/10.3390/molecules21121686
Chicago/Turabian StyleZeng, Yanning, Qaiser Mahmood, Tongling Liang, and Wen-Hua Sun. 2016. "Geometry Constrained N-(5,6,7-Trihydroquinolin-8-ylidene)arylaminopalladium Dichloride Complexes: Catalytic Behavior toward Methyl Acrylate (MA), Methyl Acrylate-co-Norbornene (MA-co-NB) Polymerization and Heck Coupling" Molecules 21, no. 12: 1686. https://doi.org/10.3390/molecules21121686