Table 1. Fine-tuning of Photocatalytic Conditionsa.
Entry | Catalyst | Solvent | Conv. |
---|---|---|---|
1 | 10 mol % Pd(OAc)2 | benzene | 100%b |
2 | 5 mol %Pd(OAc)2 | benzene | 100% |
3 | 4 mol % Pd(OAc)2 | benzene | 99% |
4 | 3 mol % Pd(OAc)2 | benzene | 89% |
5 | 2 mol % Pd(OAc)2 | benzene | 38% |
6 | 1 mol % Pd(OAc)2 | benzene | 12% |
7 | 5 mol % Pd(OAc)2 | benzene | 0%c |
8 | PdCl2 | benzene | 0% |
9 | Pd(acac)2 | benzene | 48% |
10 | Pd(TFA)2 | benzene | 83% |
11 | Pd2(dba)3 | benzene | 27% |
12 | Pd(OAc)2 | water | 7% |
13 | Pd(OAc)2 | acetone | 40% |
14 | Pd(OAc)2 | ethyl acetate | 46% |
15 | Pd(OAc)2 | THF | 83% |
16 | Pd(OAc)2 | chlorobenzene | 5% |
17 | Pd(OAc)2 | toluene | 80% |
18 | Pd(OAc)2 | BTF | 90% |
19 | Pd(OAc)2 | cyclohexane | 75% |
Standard reaction conditions: styrene (0.2 mmol), trifluoroethyl-iodide (1.5 equiv), Cs2CO3 (1.5 equiv), catalyst (5 mol %), ligand (10 mol %) in 1 mL degassed benzene under Ar atmosphere, irradiated with single 10 W 440–445 nm LEDs at 25 °C.
3 equiv of Cs2CO3 were used.
In the dark.