Table 1. Reaction Optimization*.
| Entry | Deviation from Standard Conditions | Yielda (%) | RCY (%) |
|---|---|---|---|
| 1 | with NEt3·3HF (2 equiv), 3a (1 mol%) in CH2Cl2 (0.2 M) for 16 h | 84% | |
| 2 | with KF (2 equiv), HFIP (10 equiv), 3a (1 mol%) in CH2Cl2 (0.05 M) for 16 h | 20% | |
| 3 | with CsF (2 equiv), HFIP (10 equiv), 3a (1 mol%) in CH2Cl2 (0.05 M) for 16 h | 59% | |
| 4 | none | 92 ± 4n=3 | |
| 5 | no photocatalyst | 0n=1 | |
| 6 | no irradiation | 0n=1 | |
| 7 | no HFIP | 11n=1 | |
| 8 | in THF | 51n=1 | |
| 9 | with 4CzIPN | 90n=1 | |
| 10 | 2 min reaction time | 71n=1 | |
| 11 | 0.005 mmol substrate loading | 66n=1 | |
| 12 | no N2 degassing | 82n=1 |
[18F]KF was prepared with a K2CO3 (0.011 mmol)/K222 (0.020 mmol) elution protocol. RCY: radiochemical yield determined by radioHPLC. Redox potentials given versus SCE.15
Determined by quantitative 19F NMR.
