Table 3. Catalytic Performance of Preformed Pd Complexes without Halide Ligandsa.
entry | catalyst | AgX | solvent | conv.b (%) | HAc (%) | HYd (%) |
---|---|---|---|---|---|---|
1 | 1 | AgSbF6 | acetonitrile | 84 | 56 | 8 |
2 | 1–SbF6 | acetonitrile | 100 | 50 | 2 | |
3 | 1 | AgSbF6 | neat | 100 | 58 | 11 |
4 | 1–SbF6 | neat | 90 | 60 | 3 | |
5 | 2 | AgOTf | acetonitrile | 60 | 40 | 6 |
6 | 2–OTf | acetonitrile | 45 | 28 | 5 | |
7 | 2 | AgOTf | neat | 94 | 83 | 3 |
8 | 2–OTf | neat | 97 | 64 | 2 | |
9 | 2 | AgSbF6 | acetonitrile | 77 | 41 | 18 |
10 | 2–SbF6 | acetonitrile | 53 | 29 | 4 | |
11 | 2 | AgSbF6 | neat | 95 | 89 | 0 |
12 | 2–SbF6 | neat | 100 | 62 | 0 |
Reaction conditions: 1 mmol mesitylamine, 1 mmol phenylacetylene, 0.01 mmol (1 mol %) catalyst, 2 mol % AgX, 80 °C, 25 h.
Alkyne conversion.
Yield in hydroamination product.
Yield in hydration product.