Pd(CH3CN)2Cl2/Pipecolinic Acid as a Highly Efficient Catalytic System for Suzuki-Miyaura Cross-coupling Reaction of Bromoaryl Carboxylic Acids in Water
Abstract
:1. Introduction
2. Results and Discussions
2.1. Optimization of Catalytic Conditions
2.2. Evaluation of the Scope of Pd(CH3CN)2Cl2 /L1
3. Materials and Methods
3.1. Materials
3.2. Methods
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
References
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Entry a | Ligand | Pd (mol%) | Base | Time (h) | Yield e (%) | TON f |
---|---|---|---|---|---|---|
1 | - | 0.002 | Na2CO3 | 22 | 4.9 | - |
2 | L2 | 0.002 | Na2CO3 | 22 | 6.9 | - |
3 | L3 | 0.002 | Na2CO3 | 22 | 4.0 | - |
4 | L1 | 0.002 | Na2CO3 | 6 | 95 | 4.7 × 104 |
5 | L1 | 0.002 | NaHCO3 | 6 | 94 | 4.7 × 104 |
6 | L1 | 0.002 | NaF | 6 | 24 | 1.2 × 104 |
7 | L1 | 0.002 | NaOH | 6 | 84 | 4.2 × 104 |
8 | L1 | 0.004 | Na2CO3 | 6 | 99 | 2.5 × 104 |
9 | L1 | 0.0002 | Na2CO3 | 6 | 24 | 1.2 × 105 |
10 | L1 | 0.0002 | Na2CO3 | 22 | 97 | 4.9 × 105 |
11 b | L1 | 0.0002 | Na2CO3 | 22 | 8.2 | - |
12 c | L1 | 0.0002 | Na2CO3 | 22 | 7.5 | - |
13 d | L1 | 0.0002 | Na2CO3 | 22 | <5 | - |
Entry a | Halide Fragment | Tetraarylboron Sodium Fragment | Yield d (%) | TON e |
---|---|---|---|---|
1 | 95(96) | 4.8 × 104 | ||
2 b | 98(97) | 4.9 × 104 | ||
3 | 85(72) | 4.3 × 104 | ||
4 | 96(98) | 4.8 × 104 | ||
5 | 99(96) | 5.0 × 104 | ||
6 | 86(75) | 4.3 × 104 | ||
7 | 99(97) | 5.0 × 104 | ||
8 | 98(94) | 4.9 × 104 | ||
9 | 74(40) | 3.7 × 104 | ||
10 | 95(90) | 4.8 × 104 | ||
11 b | 93(92) | 4.8 × 104 | ||
12 | 94(95) | 4.8 × 104 | ||
13 | 82(73) | 4.1 × 104 | ||
14 | 96(90) | 4.8 × 104 | ||
15 c | 99(95) | 5.0 × 104 | ||
16 b,c | 90(80) | 4.5 × 104 | ||
17 c | 97(94) | 4.9 × 104 | ||
18 c | 88(70) | 4.4 × 104 |
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Li, X.; Zhang, W.; Fu, L.; Guo, M. Pd(CH3CN)2Cl2/Pipecolinic Acid as a Highly Efficient Catalytic System for Suzuki-Miyaura Cross-coupling Reaction of Bromoaryl Carboxylic Acids in Water. Catalysts 2019, 9, 86. https://doi.org/10.3390/catal9010086
Li X, Zhang W, Fu L, Guo M. Pd(CH3CN)2Cl2/Pipecolinic Acid as a Highly Efficient Catalytic System for Suzuki-Miyaura Cross-coupling Reaction of Bromoaryl Carboxylic Acids in Water. Catalysts. 2019; 9(1):86. https://doi.org/10.3390/catal9010086
Chicago/Turabian StyleLi, Xiaogang, Wenbin Zhang, Leiqing Fu, and Mengping Guo. 2019. "Pd(CH3CN)2Cl2/Pipecolinic Acid as a Highly Efficient Catalytic System for Suzuki-Miyaura Cross-coupling Reaction of Bromoaryl Carboxylic Acids in Water" Catalysts 9, no. 1: 86. https://doi.org/10.3390/catal9010086