Table 3. Amination of Functionalized Aryl halides with Primary Alkylamine Using (CyPF-tBu)PdCl2 1a.
entry | halide | product | catalyst loading (%) | conditions | yield (%)b |
---|---|---|---|---|---|
1 | 0.05 | 100 °C 48 h | 84 | ||
2 | 0.5 | 100 °C 36 h | 52 | ||
3c | 0.5 | 110 °C 24 h | 67 | ||
4 | 0.5 | 100 °C 24 h | 77 | ||
5 | 0.5 | 100 °C 24 h | 69 | ||
6 | 0.05 | 100 °C 24 h | 84 | ||
7 | 0.05 | 100 °C 24h | 78 | ||
8c | 1.0 | 110 °C 24 h | 75 | ||
9c | 0.5 | 110 °C 24 h | 88 | ||
10c | 2.0 | 110 °C 48h | 71 | ||
11c | 1.0 | 110 °C 24 h | 85 | ||
12c | 1.0 | 110 °C 24 h | 89 |
Reactions conducted with a 1:1 ratio of metal to ligand, 1 mmol ArX, 1.2 equiv amine, and 2.4 equiv LiN(SiMe3)2 in 1 mL DME.
Isolated yield.
Using K3PO4 as the base.