Synthesis of a Ni Complex Chelated by a [2.2]Paracyclophane-Functionalized Diimine Ligand and Its Catalytic Activity for Olefin Oligomerization
Abstract
:1. Introduction
2. Results and Discussion
2.1. Preparation and Structure of Ni Complexes
2.2. Olefin Oligomerization Catalyzed by Ni Complexes
3. Conclusions
4. Experimental Section
4.1. General
4.2. Preparation of Racemic Ligand L1
4.3. Preparation of Optically Active Ligand L1
4.4. Preparation of NiBr2(L1)
4.5. X-ray Crystallography of NiBr2(L1)
4.6. Preparation of NiBr2(L2)
4.7. Oligomerization
4.7.1. Oligomerization of Ethylene
4.7.2. Oligomerization of 1-Hexene
4.7.3. Co-Dimerization of Ethylene and 1-Hexene
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Entry | Catalyst | Conditions | Products/mmol | C4TOF/h−1 b | |||
---|---|---|---|---|---|---|---|
Temp/°C | Time/h | 1-Butene | 2-Butene | Hexenes | |||
1 | NiBr2(L1) | 10 | 3 | 0.32 | 0.11 | 0.00 | 29 |
2 | NiBr2(L1) | 10 | 6 | 0.85 | 0.90 | 0.00 | 58 |
3 | NiBr2(L1) | 25 | 1 | 0.15 | 0.05 | 0.01 | 40 |
4 | NiBr2(L1) | 25 | 3 | 0.67 | 0.63 | 0.10 | 86 |
5 | NiBr2(L1) | 25 | 6 | 0.98 | 2.78 | 0.75 | 126 |
6 | NiBr2(L1) | 25 | 8 | 0.99 | 3.75 | 1.10 | 124 |
7 | NiBr2(L2) | 25 | 1 | – c | – c | – c | – c |
8 | NiBr2(L1) | 50 | 3 | 0.12 | 0.18 | 0.00 | 20 |
9 | NiBr2(L1) | 50 | 6 | 0.20 | 0.34 | 0.00 | 18 |
Entry | Co-Catalyst b | Conditions | Products (%) | C12,C18 TOF/h−1 | |||
---|---|---|---|---|---|---|---|
Temp/°C | Time/h | 2-Hexene | C12 | C18 | |||
1 | MAO (300) | 10 | 6 | 34 | 2.9 | 6.6 | 4.8 |
2 | MAO (300) | 10 | 24 | 79 | 9.5 | 8.6 | 2.3 |
3 | MAO (50) | 25 | 24 | 66 | 2.6 | 17 | 2.5 |
4 | MAO (300) | 25 | 6 | 56 | 7.3 | 13 | 10.2 |
5 | MAO (300) | 25 | 24 | 62 | 11 | 18 | 3.6 |
6 | MAO (1000) | 25 | 24 | 21 | 2.1 | 18 | 2.5 |
7 | MAO (300) | 35 | 0.5 | 33 | 4.6 | 0.0 | 28 |
8 | MAO (300) | 35 | 6 | 54 | 16 | 5.6 | 11 |
9 | MAO (300) | 35 | 24 | 45 | 22 | 28 | 6.3 |
10 | MAO (300) | 50 | 0.5 | 49 | 7.2 | 3.0 | 61 |
11 | MAO (300) | 50 | 6 | 40 | 11 | 34 | 23 |
12 | MAO (300) | 50 | 24 | 23 | 12 | 57 | 8.6 |
13 | MMAO (300) | 25 | 6 | 37 | 6.8 | 18 | 12 |
14 | AlMe3 (300) | 50 | 1 | 98 | 0.0 | 0.0 | 0.0 |
15 | Et2AlCl (300) | 50 | 1 | 95 | 0.0 | 0.0 | 0.0 |
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Takeuchi, D.; Tojo, Y.-a.; Osakada, K. Synthesis of a Ni Complex Chelated by a [2.2]Paracyclophane-Functionalized Diimine Ligand and Its Catalytic Activity for Olefin Oligomerization. Molecules 2021, 26, 2719. https://doi.org/10.3390/molecules26092719
Takeuchi D, Tojo Y-a, Osakada K. Synthesis of a Ni Complex Chelated by a [2.2]Paracyclophane-Functionalized Diimine Ligand and Its Catalytic Activity for Olefin Oligomerization. Molecules. 2021; 26(9):2719. https://doi.org/10.3390/molecules26092719
Chicago/Turabian StyleTakeuchi, Daisuke, Yoshi-aki Tojo, and Kohtaro Osakada. 2021. "Synthesis of a Ni Complex Chelated by a [2.2]Paracyclophane-Functionalized Diimine Ligand and Its Catalytic Activity for Olefin Oligomerization" Molecules 26, no. 9: 2719. https://doi.org/10.3390/molecules26092719