Ni/Co-Catalyzed Homo-Coupling of Alkyl Tosylates
Abstract
:1. Introduction
2. Results and Discussion
2.1. Screening of Reaction Conditions
2.2. Substrate Scope
2.3. Plausible Reaction Mechanism
3. Materials and Methods
3.1. General Information
3.2. General Procedure of the NiBr2phen/VB12-Catalyzed Homo-Coupling of Alkyl Tosylates
3.3. Product Characterization
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
References
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Sample Availability: Samples of the compounds are not available from the authors. |
Entry | Ni catalysts | Yield of 2a (%) a | Conversion of 1a (%) a |
---|---|---|---|
1 | NibpyCl2 | 72 | 100 |
2 b | NibpyCl2 | 0 | 20 |
3 | None | 0 | 32 |
4 c | NibpyCl2 | 0 | 0 |
5 d | NibpyCl2 | 38 | 65 |
6 | Ni(4,4’-(MeO2C)2bpy)Cl2 | 38 | 76 |
7 | Ni(4,4’-tBu2bpy)Cl2 | 18 | 67 |
8 | Ni(4,4’-Mes2bpy)Cl2 e | 38 | 78 |
9 | Ni[4,4’-(MeO)2bpy]Cl2 | 10 | 66 |
10 | Ni(6-Mebpy)Cl2 | 42 | 92 |
11 | Ni(6,6’-Me2bpy)Cl2 | 17 | 95 |
12 | Ni(1,10-phen)Cl2 | 75 | 100 |
13 | Ni(4,7-Ph2phen)Cl2 | 60 | 100 |
14 f | NiphenCl2 | 82 | 100 |
15 g | NiphenCl2 | 0 | 0 |
16 f | NiphenBr2 | 93 | 100 |
17 h | NiphenBr2 | 21–28 | 51–59 |
Entry | Alkyl Tosylates 1 | Product 2 and Yield (%) a | |||
---|---|---|---|---|---|
1 | 1b | 2b | 86 | ||
2 | 1c | 2c | 70 | ||
3 | 1d | 2d | 67 | ||
4 | 1e | 2e | 63 | ||
5 | 1f | 2f | 65 | ||
6 | 1g | 2g | 75 | ||
7 | 1h | 2h | 70 | ||
8 b | 1i | 2i | 60 | ||
9 | 1j | 2j | 73 | ||
10 | 1k | 2k | 90 [1:1] c | ||
11 d,e | 1l | 2l | 80 [1:1] c | ||
12 e, f | 1m | 2m | 65 |
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Komeyama, K.; Tsunemitsu, R.; Michiyuki, T.; Yoshida, H.; Osaka, I. Ni/Co-Catalyzed Homo-Coupling of Alkyl Tosylates. Molecules 2019, 24, 1458. https://doi.org/10.3390/molecules24081458
Komeyama K, Tsunemitsu R, Michiyuki T, Yoshida H, Osaka I. Ni/Co-Catalyzed Homo-Coupling of Alkyl Tosylates. Molecules. 2019; 24(8):1458. https://doi.org/10.3390/molecules24081458
Chicago/Turabian StyleKomeyama, Kimihiro, Ryusuke Tsunemitsu, Takuya Michiyuki, Hiroto Yoshida, and Itaru Osaka. 2019. "Ni/Co-Catalyzed Homo-Coupling of Alkyl Tosylates" Molecules 24, no. 8: 1458. https://doi.org/10.3390/molecules24081458