Optimization conditions.
Entry | Catalyst | Temperature (°C) | 2-Aminopyrimidine (equiv.) | Solvent | Yielda, % |
---|---|---|---|---|---|
1 | CuFe2O4 | 60 | 1.6 | 1,4-Dioxane | 7 |
2 | CuFe2O4 | 120 | 1.6 | 1,4-Dioxane | 66 |
3 | CuFe2O4 | 140 | 1.6 | 1,4-Dioxane | 84, 81b |
4 | CuFe2O4 | 140 | 1 | 1,4-Dioxane | 70 |
5 | CuFe2O4 | 140 | 2.3 | 1,4-Dioxane | 63 |
6 | CuFe2O4 | 140 | 1.6 | DMF | 9 |
7 | CuFe2O4 | 140 | 1.6 | DMSO | 23 |
8 | CuFe2O4 | 140 | 1.6 | Chlorobenzene | 70 |
9c | CuFe2O4 | 140 | 1.6 | 1,4-Dioxane | 0 |
10d | CuFe2O4 | 140 | 1.6 | 1,4-Dioxane | 49 |
11e | CuFe2O4 | 140 | 1.6 | 1,4-Dioxane | 15 |
12f | CuFe2O4 | 140 | 1.6 | 1,4-Dioxane | 56 |
13 | — | 140 | 1.6 | 1,4-Dioxane | 15 |
14g | CuFe2O4 | 140 | 1.6 | 1,4-Dioxane | 24 |
15 | CuI | 140 | 1.6 | 1,4-Dioxane | 38 |
16 | CuBr2 | 140 | 1.6 | 1,4-Dioxane | 58 |
17 | Cu(OAc)2 | 140 | 1.6 | 1,4-Dioxane | 34 |
18 | FeCl2 | 140 | 1.6 | 1,4-Dioxane | 67 |
19 | FeCl3 | 140 | 1.6 | 1,4-Dioxane | 41 |
20 | Fe2O3h | 140 | 1.6 | 1,4-Dioxane | 21 |
21 | CuOh | 140 | 1.6 | 1,4-Dioxane | 29 |
Trans-Chalcone (0.3 mmol), CuFe2O4 (30 μmol, 10 mol%), I2 (0.6 mmol), solvent (2.5 mL), under O2, 7 h. Yields are GC yields using diphenyl ether internal standard.
Isolated yield.
No I2.
I2 (0.45 mmol).
I2 (0.3 mmol).
CuFe2O4 (22.5 μmol, 7.5 mol%).
Under argon.
Nano oxides.