Table 2. Coupling of Aryl Halides with Primary Alkylamines Using (CyPF-tBu)PdCl2 1a.
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entry | halide | product | catalyst loading (%) | conditions | yield (%)b |
1 |
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0.001 | 110 °C, 24 h | 92 |
2 |
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0.01 | 110°C,24 h | 85 |
3 |
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0.05 | 100°C,24 h | 88 |
4 |
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0.005 | 80 °C, 36 h | 86 |
5 |
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0.005 | 100°C,36 h | 74 |
6c | 0.005 | 110 °C, 12 h | 87 | ||
7 |
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0.05 | 100°C,30 h | 88 |
8 |
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0.05 | 100°C,24 h | 96 |
9 |
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0.05 | 110 °C, 24 h | 70 |
Reactions conducted with a 1:1 ratio of metal to ligand, 1 mmol ArX, 1.2 equiv amine, and 1.4 equiv NaO-tBu in 1 mL DME.
Isolated yield.