[(PhCH2O)2P(CH3)2CHNCH(CH3)2]2PdCl2/CuI as Cocatalyst for Coupling-Cyclization of 2-Iodophenol with Terminal Alkynes in Water
Abstract
:1. Introduction
2. Results and Discussion
3. Materials and Methods
3.1. Reagents and Machine
3.2. General Experimental Procedure for the Coupling-Cyclization Reaction of 2-Iodophenol with Various Aromatic Acetylenes
3.3. Analytical Data of Products (Supplementary Materials)
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Entry | Base | CuI (mol %) | PPh3 (mol %) | Time (h) | Temperature (°C) | Yield b (%) |
---|---|---|---|---|---|---|
1 | NEt3 | 2 | 0 | 4 | 80 | 51 |
2 | NEt3 | 2 | 2 | 4 | 80 | 60 |
3 | NEt3 | 2 | 4 | 4 | 80 | 97 |
4 | NEt3 | 2 | 6 | 4 | 80 | 67 |
5 | NEt3 | 2 | 8 | 4 | 80 | 70 |
6 c | NEt3 | 0 | 4 | 4 | 80 | N.D. |
7 | NEt3 | 1 | 4 | 4 | 80 | 66 |
8 | NEt3 | 3 | 4 | 4 | 80 | 64 |
9 | NEt3 | 4 | 4 | 4 | 80 | 83 |
10 | Cs2CO3 | 2 | 4 | 4 | 80 | 28 |
11 | KOH | 2 | 4 | 4 | 80 | 19 |
12 | NaOH | 2 | 4 | 4 | 80 | 21 |
13 | Pyridine | 2 | 4 | 4 | 80 | trace |
14 | K2CO3 | 2 | 4 | 4 | 80 | trace |
15 | t-BuOH | 2 | 4 | 4 | 80 | 31 |
16 | NEt3 | 2 | 4 | 2 | 80 | 90 |
17 | NEt3 | 2 | 4 | 6 | 80 | 87 |
18 | NEt3 | 2 | 4 | 8 | 80 | 79 |
19 | NEt3 | 2 | 4 | 4 | 60 | 70 |
20 | NEt3 | 2 | 4 | 4 | 100 | 96 |
21 | NEt3 | 2 | 4 | 4 | 120 | 96 |
22 | NEt3 | 2 | 4 | 4 | 140 | 75 |
23 d | NEt3 | 2 | 4 | 4 | 80 | 53 |
24 e | NEt3 | 2 | 4 | 4 | 80 | 51 |
Entry | Alkyne | Product | Yield b (%) |
---|---|---|---|
1 | 3a | 97 | |
2 | 3b | 96 | |
3 | 3c | 95 | |
4 | 3d | 91 | |
5 | 3e | 87 | |
6 | 3f | 92 | |
7 | 3g | 78 | |
8 | 3h | 88 | |
9 | 3i | 82 | |
10 | 3j | 80 |
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Jiang, P.; Guo, M.; Fu, L.; Wen, Y.; Shen, X.; Zhou, L. [(PhCH2O)2P(CH3)2CHNCH(CH3)2]2PdCl2/CuI as Cocatalyst for Coupling-Cyclization of 2-Iodophenol with Terminal Alkynes in Water. Catalysts 2018, 8, 136. https://doi.org/10.3390/catal8040136
Jiang P, Guo M, Fu L, Wen Y, Shen X, Zhou L. [(PhCH2O)2P(CH3)2CHNCH(CH3)2]2PdCl2/CuI as Cocatalyst for Coupling-Cyclization of 2-Iodophenol with Terminal Alkynes in Water. Catalysts. 2018; 8(4):136. https://doi.org/10.3390/catal8040136
Chicago/Turabian StyleJiang, Panli, Mengping Guo, Leiqing Fu, Yongju Wen, Xiuli Shen, and Lanjiang Zhou. 2018. "[(PhCH2O)2P(CH3)2CHNCH(CH3)2]2PdCl2/CuI as Cocatalyst for Coupling-Cyclization of 2-Iodophenol with Terminal Alkynes in Water" Catalysts 8, no. 4: 136. https://doi.org/10.3390/catal8040136