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. 2019 Feb 13;9(10):5501–5511. doi: 10.1039/c9ra00097f

Optimization conditions.

graphic file with name c9ra00097f-u1.jpg
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
a

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.

b

Isolated yield.

c

No I2.

d

I2 (0.45 mmol).

e

I2 (0.3 mmol).

f

CuFe2O4 (22.5 μmol, 7.5 mol%).

g

Under argon.

h

Nano oxides.