Table 3.
Arylation of aryl chlorides with aryl aminesa
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|---|---|---|---|---|
| entry | aryl chloride | amine | product | Yield (%)b |
| 1 |
1 |
4 |
5 |
83 |
| 2 |
1 |
2 |
3 |
92 c |
| 3 |
1 |
6 |
7 |
73 |
| 4 |
1 |
8 |
9 |
86 |
| 5 |
1 |
10 |
11 |
85 |
| 6 |
1 |
12 |
13 |
65 |
| 7 |
1 |
14 |
15 |
80 |
| 8 |
1 |
16 |
17 |
85 |
| 9 |
1 |
18 |
19 |
99 |
| 10 |
1 |
20 |
21 |
96 |
| 11 |
1 |
22 |
23 |
73 |
| 12 |
1 |
24 |
25 |
84 |
| 13 |
1 |
26 |
27 |
87 |
| 14 |
1 |
28 |
29 |
99 |
| 15 |
1 |
30 |
31 |
98d |
| 16 |
32 |
24 |
33 |
99 |
| 17 |
34 |
24 |
35 |
86 |
| 18 |
36 |
24 |
37 |
85 |
Reaction conditions: 2-Chlorobenzoic acid (1.38 g, 8.83 mmol), 1.05 equiv. of amine, 1.0 equiv. of K2CO3, 9 mol% of Cu, 4 mol% of Cu2O, 3 mL of 2-ethoxyethanol and 130°C for 24 hours.
Isolated yields.
Na2CO3 was used as base.
2.0 equiv. of base were used
