Table 2. Counteranion Effect on the Catalyst Performance of Catalysts 1 and 2a.
entry | catalyst | cocatalyst | solvent | conv.b (%) | HAc (%) | HYd (%) |
---|---|---|---|---|---|---|
1 | 1 | AgPF6 | acetonitrile | 70 | 45 | 7 |
2 | 1 | AgPF6e | acetonitrile | 71 | 46 | 9 |
3 | 1 | AgNTf2 | acetonitrile | 65 | 41 | 5 |
4 | 1 | AgOTf | acetonitrile | 86 | 45 | 6 |
5 | 1 | AgOTff | acetonitrile | 51 | 31 | 2 |
6 | 1 | AgSbF6 | acetonitrile | 84 | 56 | 8 |
7 | 1 | AgSbF6 | neat | >99 | 58 | 11 |
8 | 1 | AgPF6 | neat | >99 | 68 | 3 |
9 | 1 | AgOTf | neat | 97 | 68 | 4 |
10 | 2 | AgOTf | neat | 94 | 83 | 3 |
11 | 2 | AgOTfg | neat | 95 | 87 | 3 |
12 | 2 | AgSbF6 | neat | 95 | 89 | <1 |
13 | 2 | AgSbF6g | neat | 97 | 89 | <1 |
Reaction conditions: 1 mmol mesitylamine, 1 mmol phenylacetylene, 0.01 mmol (1 mol %) catalyst, 2 mol % AgX, 1 mL solvent, 80 °C, 25 h.
Alkyne conversion.
Yield in hydroamination product.
Yield in hydration product.
4 mol % AgX.
1 mol % AgX.
3 mol % AgX.