Table 2. Gold(I)-Catalyzed Hydroamination of Ethylene by Imidazolidine-2-onea.
entry | catalyst | PC2H4 (bar) | conversion (%)b | 10:11 |
---|---|---|---|---|
1 | 1 | 4 | >99 | 100:0 |
2 | 1·MeCNc | 4 | >99 | 100:0 |
3 | 2 | 4 | 0 | - |
4 | 3 | 4 | >99 | 100:0 |
5 | 4 | 4 | <5 | n.d.d |
6 | 5 | 4 | <5 | n.d.d |
7 | 6 | 4 | 95 | 100:0 |
8 | 7 | 4 | 20 | 15:85 |
9 | 8 | 4 | >99 | 100:0 |
10 | [(Ph3P)AuCl] | 4 | 0 | |
11 | 4 | 0 | ||
12 | L1 | 4 | 0 | |
13 | L3 | 4 | 0 | |
14 | 1 | 2 | >99 | 100:0 |
15 | 1·MeCNc | 2 | 98 | 100:0 |
16 | 3 | 2 | >99 | 100:0 |
17 | 6 | 2 | 50 | 35:65 |
18 | 8 | 2 | 56 | n.d.d |
19 | 1 | 1 | 98 | 100:0 |
20 | 1·MeCNc | 1 | 50 | 35:65 |
21 | 3 | 1 | 95 | 100:0 |
22 | 6 | 1 | 11 | 10:90 |
23 | 8 | 1 | 30 | 35:65 |
24 | 1e | 1 | 64 | 30:70 |
25 | 3e | 1 | 50 | 20:80 |
26 | 1·C2H4 | 1 | >99 | 100:0 |
27 | 1f | 1 | >99 | 100:0 |
28 | 1g | 1 | 96 | 66:33 |
29 | 3f | 1 | 70 | 31:69 |
30 | 3g | 1 | 64 | 37:63 |
29 | 13 | 1 | >99 | 100:0 |
Reaction was performed with imidazolidine-2-one (0.20 mmol) under the indicated ethylene pressure, gold catalyst (0.01 mmol), and AgSbF6 (0.01 mmol) as a chloride abstractor in 1,4-dioxane (1 mL) at 100 °C for 18 h.
Conversion was determined by 1H NMR spectroscopy with anisole as the internal standard.
In the absence of AgSbF6.
Not determined (n.d).
Catalyst loading at 2 mol %.
Reaction at 80 °C.
Reaction at 60 °C.