A Well-Defined {[(PhCH2O)2P(CH3)2CHNCH(CH3)2]2PdCl2} Complex Catalyzed Hiyama Coupling of Aryl Bromides with Arylsilanes
1. Introduction
2. Results and Discussion
2.1. Optimization of the Hiyama Reaction Condition
2.2. Scope of the Substrates
3. Experimental Section
3.1. Reagents and Equipment
3.2. Synthesis of the Catalyst
3.3. General Procedure for the Synthesis
3.4. Analytical Data of Representative Products
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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- Sample Availability: Samples of the compounds {[(PhCH2O)2P(CH3)2CHNCH(CH3)2]2PdCl2} are available from the authors.
Entry | Solvent | Base | Yield (%) b |
---|---|---|---|
1 | H2O | K2CO3 | 0 |
2 | PEG | K2CO3 | 36 |
3 | PEG:H2O = 1:3 | K2CO3 | 50 |
4 | PEG:H2O = 1:1 | K2CO3 | 73 |
5 | PEG:H2O = 3:1 | K2CO3 | 64 |
6 | CH3CH2OH:H2O = 1:1 | K2CO3 | trace |
7 | PEG:H2O = 1:1 | NaOH | 85 |
8 | PEG:H2O = 1:1 | KOH | 75 |
9 | PEG:H2O = 1:1 | Et3N | 58 |
10 | PEG:H2O = 1:1 | Na2CO3 | 71 |
11 | PEG:H2O = 1:1 | K3PO4 | 62 |
12 | PEG:H2O = 1:1 | NaOAc•3H2O | 69 |
Entry | Ar-Br | Ar-Si(OMe)3 | Product | Yield (%) b |
---|---|---|---|---|
1 | | | | 88 |
2 | | | | 92 |
3 | | | | 72 |
4 c | | | | 74 |
5 c | | | | 85 |
6 c | | | | 65 |
7 c | | | | 83 |
8 c | | | | 74 |
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Guo, M.; Fu, L.; Li, J.; Zhou, L.; Kang, Y. A Well-Defined {[(PhCH2O)2P(CH3)2CHNCH(CH3)2]2PdCl2} Complex Catalyzed Hiyama Coupling of Aryl Bromides with Arylsilanes. Molecules 2016, 21, 987. https://doi.org/10.3390/molecules21080987
Guo M, Fu L, Li J, Zhou L, Kang Y. A Well-Defined {[(PhCH2O)2P(CH3)2CHNCH(CH3)2]2PdCl2} Complex Catalyzed Hiyama Coupling of Aryl Bromides with Arylsilanes. Molecules. 2016; 21(8):987. https://doi.org/10.3390/molecules21080987
Chicago/Turabian StyleGuo, Mengping, Leiqing Fu, Jiamin Li, Lanjiang Zhou, and Yanping Kang. 2016. "A Well-Defined {[(PhCH2O)2P(CH3)2CHNCH(CH3)2]2PdCl2} Complex Catalyzed Hiyama Coupling of Aryl Bromides with Arylsilanes" Molecules 21, no. 8: 987. https://doi.org/10.3390/molecules21080987