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. 2022 Mar 23;12(7):4227–4241. doi: 10.1021/acscatal.1c05823

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
a

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.

b

Conversion was determined by 1H NMR spectroscopy with anisole as the internal standard.

c

In the absence of AgSbF6.

d

Not determined (n.d).

e

Catalyst loading at 2 mol %.

f

Reaction at 80 °C.

g

Reaction at 60 °C.