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. 2020 Oct 1;22(20):8091–8095. doi: 10.1021/acs.orglett.0c03043

Table 1. Fine-tuning of Photocatalytic Conditionsa.

graphic file with name ol0c03043_0004.jpg

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%
a

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.

b

3 equiv of Cs2CO3 were used.

c

In the dark.